KR101993491B1 - Material for light emitting layers and organic electroluminescent element using same - Google Patents

Abstract

(식 중, φ 는 페닐기, 나프틸기, 페난트릴기 또는 트리페닐레닐기이고, Ar 및 Ar¹ 은 치환되어 있어도 되는 아릴이고, R 은 알킬 또는 시클로알킬이다)In an anthracene compound in which two phenyl groups are bonded at the 9-position and the 10-position shown by the following general formula (X), the 2-position and 5-position, 3-position and 4-position of one phenyl group (bonded with an anthracene at one position) An organic electroluminescent device excellent in driving voltage, luminescent efficiency and device life can be provided by using, as a material for the light emitting layer, a compound substituted with a specific aryl? At the 2-position, 4-position and 5-position.

(Wherein,? Is a phenyl group, a naphthyl group, a phenanthryl group or a triphenylenyl group, Ar and Ar ¹ are optionally substituted aryl, and R is alkyl or cycloalkyl)

Description

TECHNICAL FIELD [0001] The present invention relates to a material for a light-emitting layer and an organic electroluminescent device using the same. BACKGROUND ART [0002]

The present invention relates to an organic electroluminescent device preferable as a material for a light emitting layer of an anthracene compound, and also as a display device of a display device such as a color display. More specifically, the present invention relates to an organic electroluminescent element (hereinafter sometimes abbreviated as an organic EL element or simply an element) improved in driving voltage, luminescent efficiency and lifetime by using a specific anthracene compound in the luminescent layer.

BACKGROUND ART [0002] Organic EL devices are self-luminous type light emitting devices and are expected as display devices or light emitting devices for illumination. Recently, active research has been conducted. In order to promote the practical use of the organic EL device, the reduction of the power consumption and the longevity of the device are indispensable factors, and particularly, the blue light emitting device is a big problem.

For this reason, a variety of studies have been made on organic light emitting materials, and in order to improve the luminous efficiency and lifetime of blue light emitting devices, improvements have been made to derivatives in which various substituent groups are bonded to the basic skeleton of anthracene (for example, Patent Documents 1 to 3). Patent Document 1 discloses a light-emitting material which realizes a long life by bonding two phenyl groups to 9-position and 10 -position of an anthracene skeleton and meta-substituting various groups for one phenyl group. Patent Document 2 discloses a blue light-emitting material which realizes the same properties as the present invention by bonding a substituted / unsubstituted phenyl group and a substituted / unsubstituted naphthyl group to an anthracene skeleton. In Patent Document 3, similarly, it is also possible to use a compound in which an ortho-substituted phenyl group is connected to the 9th and 10th positions of the anthracene skeleton and the phenyl group is further substituted with a substituted amino group or a benzofuranyl group, Attempts have been made to improve device life.

Japanese Patent Laid-Open Publication No. 2000-273056 Japanese Patent Application Laid-Open No. 2006-045503 Japanese Laid-Open Patent Publication No. 2009-249551

However, sufficient characteristics can not be obtained even with the anthracene derivatives disclosed in the above-mentioned patent documents. Under such circumstances, development of a blue light emitting device improved in driving voltage, luminous efficiency, and device lifetime and a display device using the blue light emitting device has been desired.

As a result of intensive studies for solving the above problems, the present inventors have found that an anthracene compound represented by the general formula (X) (that is, the general formulas (1) to (4)) having a specific structure is used as the material for the light- , The driving voltage, the luminous efficiency and the lifetime of the device. The present invention has been completed based on this finding.

That is, the present invention provides a material for a light-emitting layer, an organic electroluminescent device, a display device having the organic electroluminescent device, and a lighting device as described below.

[1] A material for a light emitting layer containing an anthracene compound represented by the following general formula (X).

[Chemical formula 10]

In the formula (X)

is a phenyl group, a naphthyl group, a phenanthryl group or a triphenylenyl group which may be substituted with Ar ¹ and R, which is bonded to a phenyl group,

Ar is optionally substituted aryl, n is 1 or 2, Ar is bonded to either the x position or the y position when n is 1, Ar is bonded to both the x position and the y position when n is 2, Or may be the same or different in structure,

Ar ¹ is optionally substituted aryl, m is an integer which can be replaced by 0 to?, And when m is 2 or more, the structures of Ar ¹ may be the same or different,

R is independently alkyl or cycloalkyl, a is an integer of 0 to 5, b is an integer of 0 to 3, b + n is not more than 4, c is an integer that can be substituted with 0 to? m is equal to or smaller than a maximum permissible integer, d is an integer of 0 to 4,

At least one hydrogen in the anthracene compound represented by the formula (X) may be substituted with deuterium.

[2] A material for a light-emitting layer according to [1], which contains an anthracene compound represented by the following general formula (1).

(11)

In the formula (1)

Ar is optionally substituted aryl, n is 1 or 2, Ar is bonded to either the x position or the y position when n is 1, Ar is bonded to both the x position and the y position when n is 2, Or may be the same or different in structure,

Ar ¹ is optionally substituted aryl, m is an integer of 0 to 5, and when m is 2 or more, the structures of Ar ¹ may be the same or different,

R is each independently alkyl or cycloalkyl, a is an integer of 0 to 5, b is an integer of 0 to 3, b + n is 4 or less, c is an integer of 0 to 5, and c + m is 5 Or less, d is an integer of 0 to 4,

At least one hydrogen in the anthracene compound represented by the formula (1) may be substituted with deuterium.

[3] Ar is an aryl having 6 to 18 carbon atoms, which may be substituted with aryl having 6 to 18 carbon atoms, n is 1 or 2, and when n is 1, Ar is bonded to any of the x- and y- And when n is 2, Ar is bonded to both the x-position and the y-position and the structures are the same,

Ar ¹ is an aryl having 6 to 18 carbon atoms, which may be substituted with aryl having 6 to 18 carbon atoms, m is an integer from 0 to 2, m has a structure of Ar ¹ when m is 2,

R is independently an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 3 to 6 carbon atoms, a is an integer of 0 to 2, b is 0 or 1, c is an integer of 0 to 2, and d is 0 Is an integer of 2 to 2,

Wherein at least one hydrogen in the anthracene compound represented by the formula (1) may be substituted with deuterium,

The material for the light-emitting layer described in [2] above.

[4] Ar is phenyl, naphthyl, phenanthryl or triphenylenyl, which may be substituted with phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl, n is 1 or 2, n is 1 , Ar is bonded to either the x position or the y position, and when n is 2, Ar is bonded to both the x position and the y position,

Ar ¹ is phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl, which may be substituted by phenyl, naphthyl or phenanthryl, m is an integer of 0 to 2,

R is each independently methyl, ethyl, n-propyl, isopropyl, t-butyl or cyclohexyl, a is 0 or 1, b is 0 or 1, c is 0,

The material for the light-emitting layer described in [2] above.

[5] The material for a light-emitting layer according to [2], which is a compound represented by the following formula (1-1), formula (1-301) or formula (1-307).

[Chemical Formula 12]

[6] A material for a light-emitting layer according to [2], which is a compound represented by the following formula (1-3), formula (1-23), formula (1-53) or formula (1-83).

[Chemical Formula 13]

Expression (1-252), Expression (1-255), Expression (1-262), Expression (1-283), Expression (1-559) 560). ≪ / RTI >

[Chemical Formula 14]

[8] A material for a light-emitting layer according to [1], which contains an anthracene compound represented by the following general formula (2).

[Chemical Formula 15]

In the formula (2)

The naphthalene ring represented by the formula (2) is a 1-naphthyl group or a 2-naphthyl group which is bonded to a phenyl group,

Ar is optionally substituted aryl, n is 1 or 2, Ar is bonded to either the x position or the y position when n is 1, Ar is bonded to both the x position and the y position when n is 2, Or may be the same or different in structure,

Ar ¹ is optionally substituted aryl, m is an integer of 0 to 7, and when m is 2 or more, the structures of Ar ¹ may be the same or different,

R is independently alkyl or cycloalkyl, a is an integer of 0 to 5, b is an integer of 0 to 3, b + n is 4 or less, c is an integer of 0 to 7, and c + m is 7 Or less, d is an integer of 0 to 4,

At least one hydrogen in the anthracene compound represented by the formula (2) may be substituted with deuterium.

[9] The naphthalene ring represented by the formula (2) is a 1-naphthyl group or a 2-naphthyl group which is bonded to a phenyl group,

Ar is an aryl having 6 to 18 carbon atoms, which may be substituted with aryl having 6 to 18 carbon atoms; n is 1 or 2; when n is 1, Ar is bonded to either the x position or the y position; and n In this case, Ar is bonded to both the x-position and the y-position to have the same structure,

Ar ¹ is an aryl having 6 to 18 carbon atoms, which may be substituted with aryl having 6 to 18 carbon atoms, m is an integer from 0 to 2, m has a structure of Ar ¹ when m is 2,

R is independently an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 3 to 6 carbon atoms, a is an integer of 0 to 2, b is 0 or 1, c is an integer of 0 to 2, and d is 0 Is an integer of 2 to 2,

Wherein at least one hydrogen in the anthracene compound represented by the formula (2) may be substituted with deuterium,

The material for a light-emitting layer according to the above [8].

[10] The naphthalene ring represented by the formula (2) is a 1-naphthyl group or a 2-naphthyl group bonded to a phenyl group,

Ar is phenyl, naphthyl, phenanthryl or triphenylenyl, which may be substituted with phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl, n is 1 or 2, and when n is 1 Ar is bonded to either the x position or the y position, and when n is 2, Ar is bonded to both the x position and the y position,

Ar ¹ is phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl, which may be substituted by phenyl, naphthyl or phenanthryl, m is an integer of 0 to 2,

R is each independently methyl, ethyl, n-propyl, isopropyl, t-butyl or cyclohexyl, a is 0 or 1, b is 0 or 1, c is 0,

The material for a light-emitting layer according to the above [8].

[11] A material for a light-emitting layer according to [8], which is a compound represented by the following formula (2-1).

[Chemical Formula 16]

[12] The material for a light emitting layer according to [1], which contains an anthracene compound represented by the following general formula (3).

[Chemical Formula 17]

In the formula (3)

The phenanthrene ring represented by the formula (3) is a 1-, 2-, 3-, 4- or 9-phenanthryl group which is bonded to a phenyl group,

Ar is optionally substituted aryl, n is 1 or 2, Ar is bonded to either the x position or the y position when n is 1, Ar is bonded to both the x position and the y position when n is 2, Or may be the same or different in structure,

Ar ¹ is optionally substituted aryl, m is an integer of 0 to 9, and when m is 2 or more, the structures of Ar ¹ may be the same or different,

B is an integer of 0 to 3, b + n is not more than 4, c is an integer of 0 to 9, and c + m is an integer of from 9 to 9, and R is independently an alkyl or a cycloalkyl, a is an integer of 0 to 5, Or less, d is an integer of 0 to 4,

At least one hydrogen in the anthracene compound represented by the formula (3) may be substituted with deuterium.

[13] The phenanthrene ring represented by the formula (3) is a 2-, 3- or 9-phenanthryl group which is bonded to a phenyl group,

Ar is an aryl having 6 to 18 carbon atoms, which may be substituted with aryl having 6 to 18 carbon atoms; n is 1 or 2; when n is 1, Ar is bonded to either the x position or the y position; and n In this case, Ar is bonded to both the x-position and the y-position to have the same structure,

Ar ¹ is an aryl having 6 to 18 carbon atoms, which may be substituted with aryl having 6 to 18 carbon atoms, m is an integer from 0 to 2, m has a structure of Ar ¹ when m is 2,

R is independently an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 3 to 6 carbon atoms, a is an integer of 0 to 2, b is 0 or 1, c is an integer of 0 to 2, and d is 0 Is an integer of 2 to 2,

Wherein at least one hydrogen in the anthracene compound represented by the formula (3) may be substituted with deuterium,

The material for a light-emitting layer according to the above [12].

[14] The phenanthrene ring represented by the formula (3) is a 9-phenanthryl group bonded to a phenyl group,

Ar is phenyl, naphthyl, phenanthryl or triphenylenyl, which may be substituted with phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl, n is 1 or 2, and when n is 1 Ar is bonded to either the x position or the y position, and when n is 2, Ar is bonded to both the x position and the y position,

Ar ¹ is phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl, which may be substituted by phenyl, naphthyl or phenanthryl, m is an integer of 0 to 2,

R is each independently methyl, ethyl, n-propyl, isopropyl, t-butyl or cyclohexyl, a is 0 or 1, b is 0 or 1, c is 0,

The material for a light-emitting layer according to the above [12].

[15] A material for a light-emitting layer according to [1], which contains an anthracene compound represented by the following general formula (4).

[Chemical Formula 18]

In the formula (4)

The triphenylene ring represented by the formula (4) is a 1- or 2-triphenylenyl group which is bonded to a phenyl group,

Ar is optionally substituted aryl, n is 1 or 2, Ar is bonded to either the x position or the y position when n is 1, Ar is bonded to both the x position and the y position when n is 2, Or may be the same or different in structure,

Ar ¹ is optionally substituted aryl, m is an integer of 0 to 11, and when m is 2 or more, the structures of Ar ¹ may be the same or different,

R is independently alkyl or cycloalkyl, a is an integer of 0 to 5, b is an integer of 0 to 3, b + n is 4 or less, c is an integer of 0 to 11, and c + m is 11 Or less, d is an integer of 0 to 4,

At least one hydrogen in the anthracene compound represented by the formula (4) may be substituted with deuterium.

[16] The triphenylene ring represented by the formula (4) is a 1- or 2-triphenylenyl group bonded to a phenyl group,

Ar is an aryl having 6 to 18 carbon atoms, which may be substituted with aryl having 6 to 18 carbon atoms; n is 1 or 2; when n is 1, Ar is bonded to either the x position or the y position; and n In this case, Ar is bonded to both the x-position and the y-position to have the same structure,

Ar ¹ is an aryl having 6 to 18 carbon atoms, which may be substituted with aryl having 6 to 18 carbon atoms, m is an integer from 0 to 2, m has a structure of Ar ¹ when m is 2,

R is independently an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 3 to 6 carbon atoms, a is an integer of 0 to 2, b is 0 or 1, c is an integer of 0 to 2, and d is 0 Is an integer of 2 to 2,

Wherein at least one hydrogen in the anthracene compound represented by the formula (4) may be substituted with deuterium,

The material for a light-emitting layer according to the above-mentioned [15].

[17] The triphenylene ring represented by the formula (4) is a 2-triphenylenyl group bonded to a phenyl group,

Ar is phenyl, naphthyl, phenanthryl or triphenylenyl, which may be substituted with phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl, n is 1 or 2, and when n is 1 Ar is bonded to either the x position or the y position, and when n is 2, Ar is bonded to both the x position and the y position,

Ar ¹ is phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl, which may be substituted by phenyl, naphthyl or phenanthryl, m is an integer of 0 to 2,

R is each independently methyl, ethyl, n-propyl, isopropyl, t-butyl or cyclohexyl, a is 0 or 1, b is 0 or 1, c is 0,

The material for a light-emitting layer according to the above-mentioned [15].

[18] An organic electroluminescent device comprising a pair of electrodes made of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes and having the light-emitting layer material described in any one of [1] to [17] Light emitting element.

[19] The organic electroluminescent device according to the above [18], wherein the light emitting layer contains at least one selected from the group consisting of an amine having a stilbene structure, an aromatic amine derivative, and a coumarin derivative.

[20] The organic electroluminescent device according to any one of [1] to [20], further comprising an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, wherein at least one of the electron transport layer and the electron injection layer is a quinolinol metal complex, The organic electroluminescent device according to the above [18] or [19], wherein the organic electroluminescent element contains at least one selected from the group consisting of a phosphorus derivative, a phosphorus derivative, a boron derivative, a borane derivative and a benzimidazole derivative.

At least one of the electron transporting layer and the electron injecting layer may further contain at least one selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, an alkali metal halide, an alkaline earth metal oxide, The organic electroluminescent device according to the above [20], wherein the organic electroluminescent device according to the above [20], wherein the organic electroluminescent device according to the above [20], wherein the organic electroluminescent device comprises at least one selected from the group consisting of an oxide of a rare earth metal, a halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal, device.

[22] A display device comprising the organic electroluminescent device described in any one of [18] to [21] above.

[23] A lighting device comprising the organic electroluminescent device according to any one of [18] to [21].

According to a preferred embodiment of the present invention, it is possible to provide an organic electroluminescent device having a low driving voltage, a high luminous efficiency, and a long device life. Further, it is possible to provide a display device, a lighting device, and the like provided with this effective organic electroluminescent device.

1 is a schematic cross-sectional view showing an organic electroluminescent device according to this embodiment.

1. An anthracene compound represented by the general formula (X)

The anthracene compound represented by the general formula (X) can be obtained by reacting a compound represented by the general formula (1) (? = Phenyl group), a compound represented by the general formula (2) (? = A naphthyl group) = Phenanthryl group), and a compound represented by the general formula (4) (? = Triphenylenyl group).

The compound of the present invention is basically an anthracene compound in which two phenyl groups are bonded to the 9-position and the 10-position, and the 2-position, 5-position, 3-position, and 4-position of one phenyl group (bonded with an anthracene at one position) Position or 2 position, 4 position and 5 position of the aryl moiety, and by selecting such a substitution position and an aryl structure, it is a compound which achieves more excellent driving voltage, luminescent efficiency and device life as a material for a light emitting layer.

1.1 An anthracene compound represented by the general formula (1)

First, the anthracene compound represented by the general formula (1) will be described in detail. The general formula (1) is classified into the structure represented by the following formula (1a), the structure represented by the formula (1b), and the structure represented by the formula (1c).

[Chemical Formula 19]

Examples of the "aryl" of the "optionally substituted aryl" of Ar in the general formula (1) include aryl having 6 to 30 carbon atoms. Preferable " aryl " is aryl having 6 to 18 carbon atoms, more preferably aryl having 6 to 14 carbon atoms, and still more preferably aryl having 6 to 12 carbon atoms.

Specific examples of " aryl " include acenaphthylene- (1-, 3-, 4-, or 5-naphthyl) which is monocyclic aryl, phenyl, condensed bicyclic aryl, (1-, 2-, 3-, 4-, 6- or 7-membered heteroaryl), - (1-, 2-, 4-), naphthacene- (1-, 2-, 5- or 6-membered) (1-, 2-, 3-) yl, pentacene- (1-, 2-, 5-, 6-) yl which is a condensed 5-ring aryl.

As the "aryl", phenyl, naphthyl, phenanthryl, chrysenyl or triphenylenyl, and the like are preferable, and phenyl, 1-naphthyl, 2-naphthyl, And particularly preferably phenyl, 1-naphthyl or 2-naphthyl.

The substituent for " aryl " is not particularly limited as long as the desired characteristics can be obtained. Preferred examples thereof include alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, and aryl having 6 to 18 carbon atoms.

As the "alkyl having 1 to 12 carbon atoms" as the substituent, any of a linear chain and a branched chain may be used. That is, straight chain alkyl of 1 to 12 carbon atoms or branched chain alkyl of 3 to 12 carbon atoms. More preferably, it is alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms), and more preferably alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, N-propyl, isopropyl, n-butyl, isobutyl, s-butyl, isobutyl, sec-butyl Or t-butyl is preferable, and methyl, isopropyl or t-butyl is more preferable.

Specific examples of the "cycloalkyl having 3 to 12 carbon atoms" as the substituent include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl or dimethylcyclo Hexyl and the like. Among them, cyclopentyl or cyclohexyl is preferable.

As the "substituent having 6 to 18 carbon atoms" as the substituent, aryl having 6 to 14 carbon atoms is preferable, and aryl having 6 to 10 carbon atoms is particularly preferable. Specific examples thereof include phenyl, (2-, 3-, 4-) biphenyl, (1-, 2-) naphthyl, (1-, 2-, (1-, 2-) triphenylenyl, and the like.

The substituent for " aryl " is preferably indefinite. When there is a substituent, the number of substituents is, for example, the maximum number of substituents, preferably 1 to 3, more preferably 1 to 2 , And more preferably one.

The "aryl" of "aryl which may be substituted" represented by Ar ¹ in the general formula (1) includes, for example, aryl having 6 to 30 carbon atoms. Preferable " aryl " is aryl having 6 to 18 carbon atoms, more preferably aryl having 6 to 14 carbon atoms, and still more preferably aryl having 6 to 12 carbon atoms.

Specific examples of " aryl " include (2-, 3-, 4-) biphenylyl, which is monocyclic aryl, bicyclic aryl, (1-, 2-) naphthyl which is a condensed bicyclic aryl, (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1- (1-, 2-, 3-, or 4-position), which is a condensed quaternary aryl, (1-, 2-, 3-) yl, pentacene- (1- (4-methylphenyl) , 2-, 5-, 6-) yl, and the like.

As the "aryl", phenyl, biphenyl, naphthyl, phenanthryl, chrysenyl or triphenylenyl, and the like are preferable, and phenyl, 3-biphenyl, 4-biphenyl 1-naphthyl, 2-naphthyl, phenanthryl or triphenylenyl, particularly preferably phenyl, 1-naphthyl or 2-naphthyl.

The substituent for " aryl " is not particularly limited as long as the desired characteristics can be obtained. Preferred examples thereof include alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, and aryl having 6 to 18 carbon atoms.

Examples of the "alkyl having 1 to 12 carbon atoms" and "cycloalkyl having 3 to 12 carbon atoms" as the substituent include the same ones as described for the above Ar.

As the "substituent having 6 to 18 carbon atoms" as the substituent, aryl having 6 to 14 carbon atoms is preferable, and aryl having 6 to 10 carbon atoms is particularly preferable. Specific examples are phenyl, (1-, 2-) naphthyl, (1-, 2-, 3-, 4-, 9-) phenanthryl and the like.

The substituent for " aryl " is preferably indefinite. When there is a substituent, the number of substituents is, for example, the maximum number of substituents, preferably 1 to 3, more preferably 1 to 2 , And more preferably one.

The number m of the substituents of Ar ¹ is an integer of 0 to 5, preferably an integer of 0 to 2, more preferably 0 or 1.

The "alkyl" represented by R in the general formula (1) includes, for example, alkyl having 1 to 12 carbon atoms, and a detailed description thereof can be cited in the description of the above Ar.

The "cycloalkyl" represented by R in the general formula (1) includes, for example, cycloalkyl having 3 to 12 carbon atoms, and a detailed description thereof can be cited in the description of Ar in the above.

Preferably, a is an integer of 0 to 5, b is an integer of 0 to 3 (b + n is 4 or less), and c is an integer of 0 to 5 c + m is 5 or less), and d is an integer of 0 to 4. More preferably, a is an integer of 0 to 2, b is 0 or 1, c is an integer of 0 to 2, and d is an integer of 0 to 2. More preferably, a to d are zero.

The hydrogen atom in the anthracene skeleton constituting the compound represented by the general formula (1), the hydrogen atom in the phenyl group substituted at the 9-position or the 10-position of the anthracene, and the hydrogen atom in the Ar group, Ar ¹ group or R group All or some of the hydrogen atoms in the hydrogen atoms may be deuterium atoms.

Specific examples of the compound represented by the formula (1) include the following compounds represented by the following formulas (1-1) to (1-244) and (1-251) belonging to the structure represented by the formula (1a) (1-301) to (1-544), and the formulas (1-552) to (1-562) belonging to the structure represented by the formula (1b) , Compounds represented by the following formulas (1-601) to (1-612) belonging to the structure represented by the above formula (1c).

(1-12) to (1-36), (1-52) to (1-66), (1) (1-162) to (1-96), (1-112) to (1-120), (1-142) to (1-150), (1-154) 156), Expressions (1-221) to (1-244), Expressions (1-251), Expressions (1-252), Expressions (1-255), Expressions (1-261) ), Formula (1-283), Formula (1-301) to Formula (1-313), Formula (1-320) to Formula (1-333), Formula (1-352) , Expressions (1-382) to (1-396), Expressions (1-412) to (1-423), Expressions (1-442) to Expressions (1-453), Expressions (1-521) Expression (1-532), Expression (1-534) to Expression (1-542), Expression (1-559), Expression (1-560) to Expression (1-562), Expression (1-601) (1-606) are preferable, and compounds represented by the following formulas (1-1) to (1-10), (1-21) to (1-30), (1-35) 1-252) to Formula (1-60), Formula (1-221) to Formula (1-229), Formula (1-251), Formula (1-252), Formula (1-255) -261), Expression (1-262), Expression (1-283), Expression (1-301) to Expression (1-310), Expression (1-322) 352) - (1-360), (1-382) - Expression (1-390), Expression (1-412) to Expression (1-420), Expression (1-442) to Expression (1-450), Expression (1-521) (1-534) to compounds (1-542), (1-559), (1-560) to (1-562), and (1-601) Is more preferable.

[Chemical Formula 20]

[Chemical Formula 21]

[Chemical Formula 22]

(23)

≪ EMI ID =

(25)

(26)

(27)

(28)

[Chemical Formula 29]

(30)

(31)

(32)

(33)

(34)

(35)

(36)

(37)

(38)

[Chemical Formula 39]

(40)

(41)

(42)

(43)

(44)

[Chemical Formula 45]

(46)

(47)

(48)

(49)

(50)

(51)

(52)

(53)

(54)

(55)

(56)

(57)

(58)

[Chemical Formula 59]

(60)

(61)

(62)

(63)

≪ EMI ID =

(65)

1.2 An anthracene compound represented by the general formula (2)

Next, the anthracene compound represented by the general formula (2) will be described in detail. The general formula (2) is classified into a structure represented by the following formula (2a), a structure represented by the formula (2b), and a structure represented by the formula (2c). In each structure, the naphthalene ring is a 1-naphthyl group or a 2-naphthyl group.

(66)

Ar, Ar ¹ and R in the general formula (2) include those described in the general formula (1). The number of substituents m in Ar ¹ is an integer of 0 to 7, preferably an integer of 0 to 2, more preferably 0 or 1. Preferably, a is an integer of 0 to 5, b is an integer of 0 to 3 (b + n is 4 or less), and c is an integer of 0 to 7 c + m is 7 or less), and d is an integer of 0 to 4. More preferably, a is an integer of 0 to 2, b is 0 or 1, c is an integer of 0 to 2, and d is an integer of 0 to 2. More preferably, a to d are zero.

The hydrogen atom in the anthracene skeleton constituting the compound represented by the general formula (2), the hydrogen atom in the phenyl group substituted at the 9-position or the 10-position of the anthracene, the hydrogen atom in the naphthalene ring, Or all or some of the hydrogen atoms in the group represented by R < ¹ > may be deuterium.

Specific examples of the compound represented by the formula (2) include, for example, compounds represented by the following formulas (2-1) to (2-12) and (2-51) (2-62), the following formulas (2-101) to (2-112) and (2-151) to (2-162) belonging to the structure represented by the formula (2b) And the like.

(2-1) to (2-3), (2-5), (2-9) to (2-12), (2-51) -53), the equation (2-55), the equation (2-59) to the equation (2-62), the equation (2-101) to the equation (2-103), the equation (2-105) (2-112), (2-151) to (2-153), (2-155), (2-159) to (2-162) .

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1.3 General formula (3) to  The anthracene compound

Next, the anthracene compound represented by the general formula (3) will be described in detail. The general formula (3) is classified into a structure represented by the following formula (3a), a structure represented by the formula (3b), and a structure represented by the formula (3c). In each structure, the phenanthrene ring is 1-, 2-, 3-, 4- or 9-phenanthryl group.

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Ar, Ar ¹ and R in the general formula (3) include those described in the general formula (1). The number m of the substituents of Ar ¹ is an integer of 0 to 9, preferably an integer of 0 to 2, more preferably 0 or 1. Preferably, a is an integer of 0 to 5, b is an integer of 0 to 3 (b + n is 4 or less), c is an integer of 0 to 9 c + m is 9 or less), and d is an integer of 0 to 4. More preferably, a is an integer of 0 to 2, b is 0 or 1, c is an integer of 0 to 2, and d is an integer of 0 to 2. More preferably, a to d are zero.

The hydrogen atom in the anthracene skeleton constituting the compound represented by the general formula (3), the hydrogen atom in the phenyl group substituted at the 9-position or the 10-position of the anthracene, the hydrogen atom in the phenanthrene ring, All or some of the hydrogen atoms in the Ar group, Ar ¹ group or R group may be deuterium.

Specific examples of the compound represented by the formula (3) include, for example, compounds represented by the following formulas (3-1) to (3-12) belonging to the structure represented by the formula (3a) (3-51) to (3-62) belonging to the structure represented by the following formula (3).

(3-1) to (3-3), (3-5), (3-9) to (3-12), (3-51) -53), (3-55), and (3-59) to (3-62).

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1.4 An anthracene compound represented by the general formula (4)

Next, the anthracene compound represented by the general formula (4) will be described in detail. The general formula (4) is classified into the structure represented by the following formula (4a), the structure represented by the formula (4b) and the structure represented by the formula (4c). In each structure, the triphenylene ring is a 1- or 2-triphenylenyl group.

≪ EMI ID =

Ar, Ar ¹ and R in the general formula (4) include those described in the general formula (1). The number m of the substituents of Ar ¹ is an integer of 0 to 11, preferably 0 to 2, more preferably 0 or 1. Preferably, a is an integer of 0 to 5, b is an integer of 0 to 3 (b + n is 4 or less), and c is an integer of 0 to 11 c + m is 11 or less), and d is an integer of 0 to 4. More preferably, a is an integer of 0 to 2, b is 0 or 1, c is an integer of 0 to 2, and d is an integer of 0 to 2. More preferably, a to d are zero.

The hydrogen atom in the anthracene skeleton constituting the compound represented by the general formula (4), the hydrogen atom in the phenyl group substituted at the 9-position or the 10-position of the anthracene, the hydrogen atom in the triphenylene ring, , The Ar group, the Ar ¹ group or the R group may all or some of the hydrogen atoms be deuterium.

Specific examples of the compound represented by the formula (4) include, for example, compounds represented by the following formulas (4-1) to (4-12) belonging to the structure represented by the formula (4a) (4-51) to (4-62) belonging to the structure represented by the following formula (4).

(4-1) to (4-3), (4-5), (4-9) to (4-12), (4-51) -53), the formula (4-55), and the compounds represented by the formulas (4-59) to (4-62).

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[Formula 76]

2. Production method of anthracene compound represented by general formula (X)

The anthracene compound represented by the general formula (X) can be obtained by reacting a compound represented by the general formula (1) (? = Phenyl group), a compound represented by the general formula (2) (? = A naphthyl group) = Phenanthryl group), and a compound represented by the general formula (4) (? = Triphenylenyl group).

The anthracene compound represented by the formula (1) can be produced by a known synthesis method. First, the synthesis method of the anthracene compound represented by the formula (1a) will be explained as an example. The anthracene compound represented by the formula (1a) can be synthesized, for example, by the route shown in the following reaction formula (1).

First, in the reaction of the first step, the anthracene boronic acid derivative (1a-2) was subjected to Suzuki coupling reaction with the compound (1a-1) in the presence of a base using a palladium catalyst to obtain the intermediate compound (1a-3) Synthesized. Next, in the second step, a boronic acid derivative (1a-4) is subjected to a Suzuki coupling reaction with the obtained intermediate compound (1a-3) in the presence of a base using a palladium catalyst to obtain the intermediate compound (1a-5) And the boronic acid derivative (1a-6) is subjected to a Suzuki coupling reaction, whereby an anthracene compound represented by the formula (1a) of the present invention can be synthesized. Ar, Ar ¹ , R, n, m and a to d in the formula are the same as those used in formula (1).

[Formula 77]

In the reaction formula (1), the reactivity of the reactors Y ¹ and Y ^{2 in} the compound (1a-1) is made different so that the boronic acid derivatives (1a-4) and (1a-6) An anthracene compound represented by the formula (1a) can be synthesized. In the case where the boronic acid derivatives (1a-4) and (1a-6) have the same structure (for example, a compound represented by the formula (1-1)), the reactivities of the reactors Y ¹ and Y ² may be the same.

Further, by changing the position of the reactor Y ^{2 in} the compound (1a-1) or adding the reactor Y ³ in the reaction formula (1), an anthracene compound represented by the formula (1b) Can be synthesized.

Next, the reaction scheme (2), which is another reaction path, will be described. In the reaction formula (2), the anthracene boronic acid derivative (1a-2) is subjected to a Suzuki coupling reaction with a compound (1a-7) previously synthesized in the presence of a base or a commercially available product using a palladium catalyst, , An anthracene compound represented by the formula (1a) can be synthesized.

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In Scheme (2), an anthracene compound represented by formula (1b) or an anthracene compound represented by formula (1c) can be synthesized by selecting compound (1a-7) prepared in advance.

Next, the reaction scheme (3), which is another reaction route, will be described. In the reaction formula (3), a boronic acid derivative or a boronic acid ester derivative (1a-9) which has been previously synthesized in the compound (1a-8) or commercially available as a commercial product in the presence of a base using a palladium catalyst is subjected to a Suzuki coupling reaction , An anthracene compound represented by formula (1a) of the present invention can be synthesized.

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In the scheme (3), an anthracene compound represented by the formula (1b) or an anthracene compound represented by the formula (1c) can be synthesized by selecting the compound (1a-9) prepared in advance.

Specific examples of the palladium catalyst used in the Suzuki coupling reaction include tetrakis (triphenylphosphine) palladium (0): Pd (PPh ₃ ) ₄ , bis (triphenylphosphine) dichloropalladium (II): PdCl ₂ (PPh _{3) 2,} palladium acetate (II): Pd (OAc) 2, tris (dibenzylideneacetone) twenty-eight palladium _{(0): Pd 2 (dba} ) 3, tris (dibenzylideneacetone) twenty-eight palladium (0) chloroform _{complex: Pd 2 (dba) 3 ·} CHCl 3, bis (dibenzylideneacetone) palladium (0): Pd (dba) 2, bis (tri-t- butylphosphino) palladium (0): Pd (P (t of _{PdCl 2 (dppf) · CH 2} Cl 2 , such as: -Bu) _{3) 2,} or [1,1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane complex (1: 1) Can be used.

Further, in order to accelerate the reaction, a phosphine compound may be added to these palladium compounds, as the case may be. Examples of the phosphine compound include tri (t-butyl) phosphine: t-Bu ₃ P, tricyclohexylphosphine: PCy ₃ , 1- (N, N- butylphosphino) ferrocene, 1- (N, N-dibutylaminomethyl) -2- (ditertiary butylphosphino) ferrocene, 1- (methoxymethyl) -2- ) Bis (t-butylphosphino) -1,1'-binaphthyl, 2-methoxy-2 ' - (ditert-butylphosphino) -1,1'-binaphthyl, or 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl.

Specific examples of the base used in the reaction include sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogencarbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium ethoxide, sodium t-butoxide, sodium acetate, Potassium K ₃ PO ₄ , or potassium fluoride.

Examples of the solvent used in the above reaction formulas (1) to (3) include benzene, toluene, xylene, 1,2,4-trimethylbenzene, N, N-dimethylformamide, N , N-dimethylacetamide, tetrahydrofuran, diethylether, t-butylmethylether, 1,4-dioxane, methanol, ethanol, isopropylalcohol, t-butylalcohol and cyclopentylmethylether . These solvents may be used alone or as a mixed solvent. The reaction is usually carried out in a temperature range of 50 to 180 ° C, but more preferably 70 to 130 ° C.

The compounds of the present invention also include those in which at least a portion of the hydrogen atoms are substituted with deuterium. Such a compound can be synthesized in the same manner as above by using a deuterated raw material at a desired point.

The above is an explanation of the production method of the compound in which the phenyl group is selected as the? In the general formula (X) (the anthracene compound represented by the general formula (1)), but the anthracene compounds represented by the general formulas (2) And can be produced by applying the described manufacturing method. That is, the raw material compound selected so that? In the above-mentioned production method is a phenyl group can be produced by changing the raw material compound to a naphthyl group, a phenanthryl group or a phenylenyl group, respectively.

3. Organic Field  Light emitting element

The anthracene compound according to the present invention can be used, for example, as a material for an organic electroluminescent device. Hereinafter, the organic electroluminescent device according to the present embodiment will be described in detail with reference to the drawings. 1 is a schematic cross-sectional view showing an organic electroluminescent device according to this embodiment.

≪ Structure of Organic Electroluminescent Device >

1 includes a substrate 101, an anode 102 formed on the substrate 101, a hole injection layer 103 formed on the anode 102, a hole injection layer 103 formed on the anode 102, A hole transporting layer 104 formed on the electron transporting layer 103, a light emitting layer 105 formed on the hole transporting layer 104, an electron transporting layer 106 formed on the light emitting layer 105, An injection layer 107, and a cathode 108 formed on the electron injection layer 107.

The organic electroluminescent device 100 includes a substrate 101, a cathode 108 formed on the substrate 101, and an electron injection layer 102 formed on the cathode 108, for example, An electron transport layer 106 formed on the electron injection layer 107, a light emission layer 105 formed on the electron transport layer 106, a hole transport layer 104 formed on the light emission layer 105, A hole injection layer 103 formed on the transport layer 104 and an anode 102 formed on the hole injection layer 103 may be used.

The hole transport layer 104, the electron transport layer 104, and the hole transport layer 104 are formed by using the anode 102, the light emitting layer 105, and the cathode 108, 106) and the electron injection layer 107 are arbitrarily formed layers. Each of the layers may be a single layer or a plurality of layers.

The layer constituting the organic electroluminescence device may be in the form of a substrate, an anode, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a cathode in addition to the above- Anode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / cathode "," substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron "," transport layer / light emitting layer / electron transport layer / electron injection layer / cathode " Anode / hole transporting layer / light emitting layer / electron transporting layer / cathode "," substrate / anode / light emitting layer / electron transporting layer / electron injecting layer / cathode "," substrate / anode / hole transporting layer " Anode / hole injection layer / light emitting layer / electron injection layer / cathode "," substrate / anode / hole transport layer / light emitting layer / electron transport layer / cathode " Hole injection layer / light emitting layer / electron transporting layer / cathode "," substrate / anode / light emitting layer / electron transporting layer / cathode " Cathode / light emitting layer / electron injection layer / cathode ".

≪ Substrate in Organic Electroluminescent Device >

The substrate 101 serves as a support for the organic electroluminescent device 100, and typically quartz, glass, metal, plastic, or the like is used. The substrate 101 is formed into a plate shape, a film shape, or a sheet shape, depending on the purpose. For example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Among them, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, polysulfone and the like are preferable. As the glass substrate, soda lime glass, alkali-free glass, or the like is used. In addition, the thickness is required to be sufficient to maintain the mechanical strength. For example, it may be 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. With respect to the material of the glass, since it is preferable that the elution ions from the glass are small, the non-alkali glass is preferable, but since soda lime glass which is subjected to barrier coating such as SiO _{2 is} also commercially available, it can be used. A gas barrier film such as a dense silicon oxide film may be formed on at least one surface of the substrate 101 in order to enhance the gas barrier property. In particular, a plate, film or sheet made of synthetic resin having low gas barrier property may be formed on the substrate 101 ), It is preferable to form a gas barrier film.

≪ Positive electrode in organic electroluminescent device >

The anode 102 serves to inject holes into the light emitting layer 105. [ When the hole injecting layer 103 and / or the hole transporting layer 104 are formed between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through the hole injecting layer 103 and / or the hole transporting layer 104.

Examples of the material for forming the anode 102 include an inorganic compound and an organic compound. Examples of the inorganic compound include metals (aluminum, gold, silver, nickel, palladium, chromium and the like), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO) ), A halogenated metal (copper iodide, etc.), sulfur dioxide, carbon black, ITO glass, and Nessa glass. Examples of the organic compound include polythiophene such as poly (3-methylthiophene), conductive polymer such as polypyrrole, polyaniline, and the like. In addition, it can be appropriately selected from the materials used as the anode of the organic electroluminescent device.

The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for light emission of the light emitting element, but it is preferable that the resistance is low in view of power consumption of the light emitting element. For example, an ITO substrate of 300 OMEGA / & squ & or less functions as an element electrode, but it is possible to supply a substrate of about 10 OMEGA / It is particularly preferable to use a low resistance product of 50 to 5? / ?. Thickness of ITO can be arbitrarily selected in accordance with the resistance value, but is usually used in a range of 50 to 300 nm.

≪ Hole injection layer and hole transport layer in organic electroluminescent device >

The hole injection layer 103 serves to efficiently inject holes moving from the anode 102 into the light emitting layer 105 or into the hole transport layer 104. The hole transport layer 104 serves to efficiently transport the holes injected from the anode 102 or the holes injected from the anode 102 through the hole injection layer 103 to the light emitting layer 105. Each of the hole injecting layer 103 and the hole transporting layer 104 is formed of a mixture of one or more kinds of hole injecting and transporting materials or a mixture of a hole injecting and transporting material and a polymer binder. An inorganic salt such as iron (III) chloride may be added to the hole injecting and transporting material to form a layer.

As the hole injecting and transporting material, it is necessary to efficiently inject and transport holes from the positive electrode between the electrodes to which an electric field is applied, and it is desired that the hole injecting efficiency is high and the injected holes are efficiently transported. For this purpose, it is preferable that the material has a low ionization potential, a high hole mobility, an excellent stability, and an impurity which is a trap, which does not readily occur during production and use.

As the material for forming the hole injecting layer 103 and the hole transporting layer 104, a hole injecting layer of a p-type semiconductor, a hole injecting layer of an organic electroluminescent device, a compound which is conventionally used as a hole transporting material in a photoconductive material, And a known hole transporting layer may be selected and used. Specific examples thereof include biscarbazole derivatives such as carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole and the like), bis (N-arylcarbazole) and bis (N-alkylcarbazole), triarylamine derivatives (Polymer having an aromatic tertiary amino group as a main chain or side chain, 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane, N, N'- Methylphenyl) -4,4'-diaminobiphenyl, N, N'-diphenyl-N, N'-dinaphthyl-4,4'- diaminobiphenyl, N, Di (3-methylphenyl) -4,4'-diphenyl-1,1'-diamine, N, N'-dinaphthyl-N, N'-diphenyl- Triphenylamine derivatives such as phenyl-1,1'-diamine, 4,4 ', 4 "-tris (3-methylphenyl (phenyl) amino) triphenylamine and starburst amine derivatives), stilbene derivatives, phthalocyanine derivatives (Metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, A cyclic compound such as a cyclopentane derivative, a cyclic compound such as a cyclopentane derivative, a cyclopentane derivative, a cyclopentane derivative, a cyclopentane derivative and a cyclopentane derivative. And is capable of injecting holes from the anode, and is capable of transporting holes, is not particularly limited.

It is also known that the conductivity of the organic semiconductor is strongly influenced by its doping. Such an organic semiconductor matrix material is composed of a compound having a good electron acceptor or a compound having a good electron accepting property. For doping the electron donor, a strong electron acceptor such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) 73 (22), 3202-3204 (1998), and in J. Blochwitz, J. < RTI ID = 0.0 > , M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73 (6), 729-731 (1998)]. These produce so-called holes by the electron transfer process in the electron donor type base material (hole transport material). Depending on the number of holes and the degree of mobility, the conductivity of the base material changes relatively largely. As the matrix material having a hole transporting property, for example, a benzidine derivative (TPD), a starburst amine derivative (TDATA or the like), or a specific metal phthalocyanine (in particular, zinc phthalocyanine ZnPc or the like) 2005-167175).

≪ Light Emitting Layer in Organic Electroluminescent Device >

The light emitting layer 105 emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. As a material for forming the light emitting layer 105, a compound (luminescent compound) that excites by the recombination of holes and electrons to emit light can be used, and a stable thin film shape can be formed. Further, Or a compound represented by the formula In the present invention, a compound represented by the general formula (X) (that is, the general formulas (1) to (4)) can be used as the material for the light emitting layer.

The light-emitting layer may be a single layer, a plurality of layers, or both, and each of the light-emitting layers is formed of a light-emitting layer material (host material, dopant material). Each of the host material and the dopant material may be one type or a combination of two or more. The dopant material may be included in the entire host material, partially included, or any of them. As a doping method, it can be formed by a co-evaporation method with a host material, but it may be vapor-deposited at the same time after it is mixed with a host material in advance.

The amount of the host material to be used differs depending on the kind of the host material and may be determined according to the characteristics of the host material. The amount of the host material used is preferably from 50 to 99.999% by weight, more preferably from 80 to 99.95% by weight, and still more preferably from 90 to 99.9% by weight of the entire material for the light emitting layer. The compound represented by the general formula (X) (that is, the general formulas (1) to (4)) according to the present invention is preferably a host material.

The amount of the dopant material to be used differs depending on the kind of the dopant material and may be determined in accordance with the characteristics of the dopant material. The amount of the dopant to be used is preferably from 0.001 to 50% by weight, more preferably from 0.05 to 20% by weight, and still more preferably from 0.1 to 10% by weight based on the total weight of the light emitting layer material. The above range is preferable from the viewpoint of, for example, preventing concentration quenching phenomenon.

Examples of the host material that can be used in combination with the compound represented by the general formula (X) (that is, the general formulas (1) to (4)) according to the present invention include condensed ring derivatives such as anthracene and pyrene, A bisstyryl derivative such as a bisstyryl anthracene derivative or a distyryl benzene derivative, a tetraphenyl butadiene derivative, a cyclopentadiene derivative, a fluorene derivative, and a benzofluorene derivative.

The dopant material is not particularly limited, and any known compound can be used, and it can be selected from various materials according to a desired luminescent color. Specific examples thereof include condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene and chrysene, benzoxazole derivatives, benzothiazole A thiazole derivative, an imidazole derivative, a thiadiazole derivative, a triazole derivative, a pyrazoline derivative, a stilbene derivative, a thiophene derivative, a thiophene derivative, (Japanese Unexamined Patent Application, First Publication No. 1-245087), bisstyrylarylene derivatives (Japanese Unexamined Patent Publication No. Hei 1-245087) such as tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyryl anthracene derivatives and distyryl benzene derivatives 2-247278), diazinedasene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, dim mesityl isobenzofuran, di (2-methylphenyl) isobenzofuran, di Isobenzofuran derivatives such as isobenzofuran and phenyl isobenzofuran, dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7- Benzimidazolylcoumarin derivatives, coumarin derivatives such as 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiophene derivatives such as 3-benzoimidazolylcoumarin derivatives, 3-benzothiazolylcoumarin derivatives, A pyrimidine derivative, a pyrazine derivative, a carbostyril derivative, an acridine derivative, an oxazine derivative, a phenylene oxide derivative, a pyrimidine derivative, a pyrimidine derivative, a cyanine derivative, an oxobenzoanthracene derivative, Quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, propylidine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyromethene derivatives There may be mentioned, for example, a metal complex, a metal complex, a conductor, a perinone derivative, a pyrrolopyrrole derivative, a squarylium derivative, a viololtron derivative, a phenazine derivative, an acridone derivative, a diazaflavine derivative, a fluorene derivative and a benzofluorene derivative.

Examples of the blue to cyan dopant materials include aromatic hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene and chrysene, derivatives thereof, And examples thereof include thiophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, Aromatic heterocyclic compounds or derivatives thereof such as naphthylidine, quinoxaline, pyrrolopyridine and thioxanthone, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, imidazoles, thiazoles , Azido derivatives such as thiadiazole, carbazole, oxazole, oxadiazole and triazole, and metal complexes thereof and N, N'-diphenyl-N, N'-di (3-methylphenyl) Aromatic amine derivatives represented by diphenyl-1,1'-diamine and the like There.

Examples of the rust-yellow dopant material include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, And a naphthacene derivative such as a naphthacene derivative such as a naphthacene derivative represented by the formula (1), and a substituent capable of long wavelength, such as an aryl group, a heteroaryl group, an arylvinyl group, an amino group or a cyano group, The compound is also a preferable example.

Examples of the back-to-red dopant materials include naphthalimide derivatives such as bis (diisopropylphenyl) perylenetetracarboxylic acid imide, perynone derivatives, and derivatives of acetylacetone, benzoyl acetone and phenanthroline, which are ligands Eu complex, a metal phthalocyanine derivative such as 4- (dicyanomethylene) -2-methyl-6- (p-dimethylaminostyryl) -4H-pyran or a derivative thereof, magnesium phthalocyanine, aluminum chlorophthalocyanine, A pyrazine derivative, a pyrazine derivative, a pyrazine derivative, a pyrazine derivative, a pyrazine derivative, a pyrazine derivative, a pyrazine derivative, a pyrazine derivative, a pyrazine derivative, a pyrazine derivative, A thiadiazole derivative, a thiadiazole derivative, a thiadiazole derivative, a thiadiazole derivative, a thiadiazole derivative, a thiadiazole derivative, a thiadiazole derivative and a thiadiazole pyrene derivative. A compound having a substituent capable of making a long wavelength such as a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group, a hydroxyl group,

In addition, the dopant can be appropriately selected from compounds described in Chemical Industry 2004, June 2004, page 13, and the references cited therein.

Of the dopant materials described above, an amine having a stilbene structure, a perylene derivative, a borane derivative, an aromatic amine derivative, a coumarin derivative, a pyran derivative or a pyrene derivative is preferable.

An amine having a stilbene structure is represented by the following formula, for example.

(80)

Of the art formula, Ar ¹ is a m-valent group derived from a aryl having 6 to 30 carbon atoms, Ar ² and Ar ³ are, each independently, but an aryl having 6 to 30 carbon atoms, and at least one of Ar ¹ ~ Ar ³ is steel Benz structure, Ar ¹ to Ar ³ may be substituted, and m is an integer of 1 to 4.

The amine having a stilbene structure is more preferably a diaminostilbene represented by the following formula.

[Formula 81]

In the formulas, Ar ² and Ar ³ are each independently aryl having 6 to 30 carbon atoms, and Ar ² and Ar ³ may be substituted.

Specific examples of aryl having 6 to 30 carbon atoms include benzene, naphthalene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, perylene, Benzyl, distyrylbenzene, distyrylbiphenyl, distyrylfluorene, and the like.

Specific examples of the amines having a stilbene structure include N, N, N ', N'-tetra (4-biphenyl) -4,4'-diaminostilbene, N, N ', N'-tetra (2-naphthyl) -4,4'-diaminostilbene, N, -Di (2-naphthyl) -N, N'-diphenyl-4,4'-diaminostilbene, N, N'- Bis [4'-bis (diphenylamino) styryl] - 4'-diaminostilbene, 4,4'-bis [ Benzene, 2,7-bis [4'-bis (diphenylamino) styryl] -9,9-dimethylfluorene, 4,4'- , 4,4'-bis (9-phenyl-3-carbazovinylene) -biphenyl, and the like.

In addition, amines having a stilbene structure described in JP-A-2003-347056 and JP-A-2001-307884 may be used.

Examples of the perylene derivatives include 3,10-bis (2,6-dimethylphenyl) perylene, 3,10-bis (2,4,6-trimethylphenyl) perylene, Perylene, 3,4-diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3- (1'-pyrenyl) Di (t-butyl) perylene, 3- (9'-anthryl) -8,11- t-butyl) perylenyl), and the like.

Japanese Laid-Open Patent Publication No. 11-97178, Japanese Laid-Open Patent Publication No. 2000-133457, Japanese Laid-Open Patent Publication No. 2000-26324, Japanese Laid-Open Patent Publication No. 2001-267079, Japanese Laid-Open Patent Publication No. 2001-267078, Perylene derivatives described in Patent Publications 2001-267076, 2000-34234, 2001-267075, and 2001-217077 may be used.

Examples of the borane derivative include 1,8-diphenyl-10- (dimethyisilbyl) anthracene, 9-phenyl-10- (dimethyisilbyl) anthracene, 4- (9'- Mesitylborylnaphthalene, 4- (10'-phenyl-9'-anthryl) dimethyisiloborylnaphthalene, 9- (dimethyisilbyl) anthracene, 9- Mesitylbutyl) anthracene, and 9- (4 '- (N-carbazolyl) phenyl) -10- (dimethyisilbyl) anthracene.

Borane derivatives described in WO 2000/40586 pamphlet and the like may also be used.

An aromatic amine derivative is represented by the following formula, for example.

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In the formulas, Ar ⁴ is an n-valent group derived from aryl having 6 to 30 carbon atoms, Ar ⁵ and Ar ⁶ are each independently aryl having 6 to 30 carbon atoms, Ar ⁴ to Ar ⁶ may be substituted, , and n is an integer of 1 to 4.

Particularly, Ar ⁴ is an anthracene, chrysene or pyrene derived bivalent group, Ar ⁵ and Ar ⁶ are each independently aryl having 6 to 30 carbon atoms, Ar ⁴ to Ar ⁶ may be substituted, and n And an aromatic amine derivative is more preferable.

Specific examples of the aryl having 6 to 30 carbon atoms include benzene, naphthalene, acenaphthylene, fluorenenal, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, perylene, pentacene And the like.

Examples of the aromatic amine derivatives include N, N, N ', N'-tetraphenylchrysene-6,12-diamine, N, N, N' N, N ', N'-tetrakis (m-tolyl) chrysene-6,12-diamine, N, -Isopropylphenyl) chrysene-6,12-diamine, N, N, N ', N'-tetra (naphthalene- N, N'-bis (4-ethylphenyl) chrysene-6,12-diamine, N, N'- Bis (4-ethylphenyl) chrysene-6,12-diamine, N, N'-diphenyl-N, N'- N, N'-bis (4-t-butylphenyl) chrysene-6,12-diamine, N, ) -N, N'-di (p-tolyl) chrysene-6,12-diamine.

The pyrene system may be, for example, N, N, N ', N'-tetraphenylpyrene-1,6-diamine, N, N, N', N'-tetra (p- Diamine, N, N, N ', N'-tetrakis (4-isopropylphenyl) pyrene-1 , 6-diamine, N, N, N ', N'-tetrakis (3,4-dimethylphenyl) N, N'-bis (4-ethylphenyl) pyrene-1,6-diamine, N, N'- N, N'-bis (4-ethylphenyl) pyrene-1,6-diamine, N, N'- (4-t-butylphenyl) pyrene-1,6-diamine, N, N'-bis (4-isopropylphenyl) -N, N'- Diamine, N, N, N ', N'-tetrakis (3,4-dimethylphenyl) -3,8-diphenylpyrene-1,6-diamine and the like.

Examples of the anthracene-based anthracene compound include N, N, N, N-tetraphenyl anthracene-9,10-diamine, N, N, N ', N'-tetra (p- Diamine, N, N, N ', N'-tetrakis (4-isopropylphenyl) anthracene-9,10 Diamine, N, N'-diphenyl-N, N'-di (p-tolyl) anthracene-9,10- -9,10-diamine, N, N'-diphenyl-N, N'-bis (4-ethylphenyl) anthracene-9,10- (4-ethylphenyl) anthracene-9,10-diamine, N, N'-diphenyl-N, N'- N, N'-bis (4-t-butylphenyl) anthracene-9,10-diamine, N, N'- Di-t-butyl-N, N, N ', N'-tetra (p- tolyl) anthracene-9,10- diamine, 2,6- , N'-bis (4-isopropylphenyl) anthracene-9,10-diamine, 2,6- (4-isopropylphenyl) -N, N'-di (p-tolyl) anthracene-9,10-diamine, 2,6- Di (p-tolyl) anthracene-9,10-diamine, 2,6-dicyclohexyl-N, N'-bis (4-isopropylphenyl) ) Anthracene-9,10-diamine, 9,10-bis (4-diphenylamino-phenyl) anthracene, 9,10- Di-p-tolylamino-9- (4-di-p-tolylamino-1-naphthyl) anthracene, 10-diphenylamino-9 - (4-diphenylamino-1-naphthyl) anthracene, and 10-diphenylamino-9- (6-diphenylamino-2-naphthyl) anthracene.

Also, the pyrene-based compound may be, for example, N, N, N, N-tetraphenyl-1,8-pyrene-1,6-diamine, N- Diamine, N ¹ , N ⁶ -diphenyl-N ¹ , N ⁶ -bis- (4-trimethylsilanyl-phenyl) -1H, 8H-pyrene-1,6- have.

In addition, in addition to the above, it is also possible to use other compounds such as [4- (4-diphenylamino-phenyl) naphthalen-1-yl] Bis [4-diphenylaminophthalen-1-yl] biphenyl, 4,4'-bis [ 4-diphenylamino naphthalene-2-yl] -p-terphenyl, and the like.

An aromatic amine derivative described in JP-A-2006-156888 may also be used.

Examples of coumarin derivatives include coumarin-6 and coumarin-334.

Further, coumarin derivatives described in JP-A-2004-43646, JP-A-2001-76876, JP-A-6-298758, and the like may be used.

Examples of the pyran derivative include DCM and DCJTB described below.

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In addition, Japanese Unexamined Patent Application Publication Nos. 2005-126399, 2005-097283, 2002-234892, 2001-220577, 2001-081090, and Japanese Unexamined Patent Publication A pyran derivative described in Patent Publication No. 2001-052869 may be used.

≪ Electron injection layer and electron transport layer in organic electroluminescent device >

The electron injection layer 107 serves to efficiently inject electrons moving from the cathode 108 into the light emitting layer 105 or into the electron transporting layer 106. The electron transporting layer 106 serves to efficiently transport electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light emitting layer 105. The electron transporting layer 106 and the electron injecting layer 107 are each formed of a mixture of one or more kinds of electron transporting / injecting materials, or a mixture of an electron transporting / injecting material and a polymer binder.

The electron injecting and transporting layer is a layer which injects electrons from a cathode and transports electrons. The electron injecting and transporting layer is required to efficiently transport injected electrons with high electron injection efficiency. For this purpose, it is preferable that the electron affinity is large, the electron mobility is high, the stability is excellent, and the impurities which become the trap do not occur at the time of production and use. However, in the case of considering the transport balance of holes and electrons, in the case of mainly taking charge of effectively preventing the holes from the anode from flowing to the cathode side without recombination, The effect of improving is equivalent to that of a material having a high electron transporting ability. Therefore, the electron injecting and transporting layer in the present embodiment may also include the function of a layer capable of effectively blocking the movement of holes.

Examples of the material (electron transporting material) for forming the electron transporting layer 106 or the electron injecting layer 107 include a compound conventionally used as an electron transporting compound in a photoconductive material, an electron injecting layer of an organic electroluminescent device, Can be arbitrarily selected from known compounds used in the art.

Examples of the material used for the electron transporting layer or the electron injecting layer include compounds containing an aromatic ring or a heterocyclic ring composed of at least one atom selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus, pyrrole derivatives and condensed ring derivatives thereof And a metal complex having an electron-accepting nitrogen. Specifically, condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4'-bis (diphenylethenyl) biphenyl, perinone derivatives, coumarin derivatives, naphthalimide Derivatives thereof, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, carbazole derivatives and indole derivatives. Examples of the metal complex having electron-accepting nitrogen include a hydroxyazole complex such as a hydroxyphenyloxazole complex, an azomethine complex, a tropolone metal complex, a flavonol metal complex, and a benzoquinoline metal complex . These materials may be used alone, but they may be mixed with different materials.

Specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, (4-t-butylphenyl) 1,3,4-oxadiazolyl] phenylene), a thiophene derivative, a triazole derivative (N- Naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, (Benzo [h] quinolin-2-yl) -9,9 ', 6'-benzopyranone derivatives, - spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives Benzophenone derivatives, benzophenone derivatives, tris (N-phenylbenzoimidazol-2-yl) benzene), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, Bis (4 '- (2,2': 6'2 "-terpyridinyl)) benzene), a naphthyridine derivative (bis (1-naphthyl) -4- (1,8-naphthyridin- 2-yl) phenylphosphine oxide, etc.), aldazine derivatives, carbazole derivatives, indole derivatives, phosphorus oxide derivatives, and bisstyryl derivatives.

Further, a metal complex having electron-accepting nitrogen may be used. For example, a hydroxyazole complex such as a quinolinol-based metal complex or a hydroxyphenyloxazole complex, an azomethine complex, a tropolone metal complex, a flavonol metal complex And benzoquinoline metal complexes.

The above-described materials may be used singly, but they may be mixed with different materials.

Of the above-described materials, quinolinol-based metal complexes, bipyridine derivatives, phenanthroline derivatives or borane derivatives are preferred.

The quinolinol-based metal complex is a compound represented by the following formula (E-1).

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In the formulas, R ¹ to R ⁶ are hydrogen or a substituent, M is Li, Al, Ga, Be or Zn, and n is an integer of 1 to 3.

Specific examples of the quinolinol-based metal complexes include 8-quinolinolithium, tris (8-quinolinolato) aluminum, tris (4-methyl-8- quinolinolato) Quinolinolato) aluminum, tris (3,4-dimethyl-8-quinolinolato) aluminum, tris (4,5- (2-methyl-8-quinolinolate) aluminum (bis (2-methyl-8-quinolinolate) aluminum Aluminum, bis (2-methyl-8-quinolinolate) (4-methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2-methyl-8-quinolinolate) (3-phenylphenolate) aluminum, bis (2-methyl- (4-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate (2-methyl-8-quinolinolate) aluminum (2,2-dimethylphenolate) aluminum, bis (2-methyl- (3,5-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-methyl-8-quinolinolate) Aluminum, bis (2-methyl-8-quinolinolate) (2,6-diphenylphenolate) aluminum, bis Aluminum (2,4,6-triphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) Aluminum, bis (2-methyl-8-quinolinolate) (1-naphtholate) aluminum, bis (2-naphtholate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (2-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2,4- (3,5-dimethylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-di- (2-methyl-8-quinolinolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) aluminum-.mu.- (2-methyl-4-ethyl-8-quinolinolate) aluminum-? -Oxo-bis (2-methyl- Ethyl-8-quinolinolate) aluminum, bis (2-methyl-4-methoxy-8- quinolinolate) aluminum- (2-methyl-5-cyano-8-quinolinolate) aluminum,? -Oxo-bis (2- (2-methyl-5-trifluoromethyl-8-quinolinolate) aluminum, bis (10-hydroxy-5-trifluoromethyl- Benzo [h] quinoline) beryllium and the like.

The bipyridine derivative is a compound represented by the following formula (E-2).

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In the formulas, G represents a simple bonding hand or an n-valent connecting group, and n is an integer of 2 to 8. The carbon atom which is not used for the coupling of pyridine-pyridine or pyridine-G may be substituted.

Examples of G in the general formula (E-2) include the following structural formulas. In the following formulas, R's are each independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenyl or terphenyl.

≪ EMI ID =

Specific examples of pyridine derivatives include 2,5-bis (2,2'-pyridin-6-yl) -1,1-dimethyl-3,4-diphenylsilole, 2,5- (2,2'-pyridin-5-yl) -1,1-dimethyl-3,4-dimethyl-3,4-dimethylaniline (2,2'-pyridin-5-yl) -1,1-dimethyl-3,4-dimemethylsilylol, 9,10-di (2,3'-pyridin-6-yl) anthracene, 9,10-di (2,2'- (2,3'-pyridin-5-yl) anthracene, 9,10-di (2,3'- (2,2'-pyridin-5-yl) -2-phenylanthracene, 9,10- (2,4'-pyridin-5-yl) -2-phenyl-2-phenyl- Anthracene, 9,10-di (3,4'-pyridin-6-yl) -2-phenylanthracene, 9,10- (2,2'-pyridin-6-yl) thiophene, 3,4-diphenyl-2,5-di (2,3'- Naphthyridin-5-yl) thiophene, 6'6 "- di (2-pyridyl) 2,2 ': 4', 4": 2 ", 2" '-, and the like quarter pyridine.

The phenanthroline derivative is a compound represented by the following formula (E-3-1) or (E-3-2).

[Chemical Formula 87]

In the formulas, R ¹ to R ⁸ are each a hydrogen or a substituent, adjacent groups may be bonded to each other to form a condensed ring, G represents a simple bond or an n-valent connecting group, and n is an integer of 2 to 8. Examples of G in the general formula (E-3-2) include the same ones described in the paragraph of the bipyridine derivative.

Specific examples of phenanthroline derivatives include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10- Di (1,10-phenanthroline-2-yl) anthracene, 2,6-di (1,10-phenanthroline-5-yl) pyridine, 1,3,5- 5-yl) benzene, 9,9'-difluoro-bis (1,10-phenanthroline- Phenanthroline-9-yl) benzene and the like.

Particularly, a case where a phenanthroline derivative is used for an electron transport layer and an electron injection layer will be described. In order to obtain stable luminescence over a long period of time, a material having excellent thermal stability and thin film formability is desired, and among the phenanthroline derivatives, the substituent itself has a three-dimensional three-dimensional structure, or a phenanthroline skeleton, Dimensional steric structure or a plurality of phenanthroline skeletons are connected to each other by a three-dimensional repulsion. Further, when a plurality of phenanthroline skeletons are connected, a compound containing conjugated bonds, substituted or unsubstituted aromatic hydrocarbons, and substituted or unsubstituted aromatic heterocyclic rings is more preferable in the connecting unit.

The borane derivative is a compound represented by the following formula (E-4), specifically disclosed in Japanese Patent Application Laid-Open No. 2007-27587.

[Formula 88]

Wherein, R ¹¹ and R ¹² are, each independently, a hydrogen atom, an alkyl group, an aryl group that may be substituted, a substituted silyl group, a nitrogen which may be substituted containing heterocyclic group, or a numbered, at least one of a cyano group, R ¹³ ~ R ¹⁶ is each independently a substituted or unsubstituted alkyl group or an optionally substituted aryl group; X is an optionally substituted arylene group; and Y is an optionally substituted aryl group having up to 16 carbon atoms, substituted boryl group , Or a carbazole group which may be substituted, and n is independently an integer of 0 to 3.

Among the compounds represented by the above general formula (E-4), the compounds represented by the following general formula (E-4-1), the following general formulas (E-4-1-1) to (E- Are preferred. Specific examples include 9- [4- (4-dimetylthiophenylboranaphthalen-1-yl) phenyl] carbazole, 9- [4- Yl] carbazole and the like.

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Wherein, R ¹¹ and R ¹² are, each independently, a hydrogen atom, an alkyl group, an aryl group that may be substituted, a substituted silyl group, a nitrogen which may be substituted containing heterocyclic group, or a numbered, at least one of a cyano group, R ¹³ ~ R ¹⁶ are, each independently, an aryl group that may be substituted with an alkyl group, or substituted optionally, R ²¹ and R ²² are, each independently, a hydrogen atom, an alkyl group, a substituted aryl group, an optionally substituted silyl group, an optionally substituted, respectively X ¹ is an arylene group having 20 or less carbon atoms which may be substituted, n is independently an integer of 0 to 3, and m is independently an integer of 0 to 3, And is an integer of 0 to 4.

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In the formulas, R ³¹ to R ³⁴ are each independently methyl, isopropyl or phenyl, and R ³⁵ and R ³⁶ are each independently hydrogen, methyl, isopropyl or phenyl.

Among the compounds represented by the general formula (E-4), the compounds represented by the following formula (E-4-2) and the compounds represented by the following formula (E-4-2-1) are preferable.

[Formula 91]

Wherein, R ¹¹ and R ¹² are, each independently, a hydrogen atom, an alkyl group, an aryl group that may be substituted, a substituted silyl group, a nitrogen which may be substituted containing heterocyclic group, or a numbered, at least one of a cyano group, R ¹³ ~ R ¹⁶ is independently an alkyl group which may be substituted or an aryl group which may be substituted, X ¹ is an optionally substituted arylene group having 20 or less carbon atoms, and n is independently an integer of 0 to 3 to be.

≪ EMI ID =

Wherein R ³¹ to R ³⁴ are each independently methyl, isopropyl or phenyl, and R ³⁵ and R ³⁶ are each independently hydrogen, methyl, isopropyl or phenyl.

Among the compounds represented by the general formula (E-4), the compounds represented by the following general formula (E-4-3), the compounds represented by the general formulas (E-4-3-1) Are preferred.

≪ EMI ID =

Wherein, R ¹¹ and R ¹² are, each independently, a hydrogen atom, an alkyl group, an aryl group that may be substituted, a substituted silyl group, a nitrogen which may be substituted containing heterocyclic group, or a numbered, at least one of a cyano group, R ¹³ ~ R ¹⁶ is each independently a substituted or unsubstituted alkyl group or an optionally substituted aryl group; X ¹ is an optionally substituted arylene group having 10 or less carbon atoms; and Y ¹ is a substituted or unsubstituted And n is an integer of 0 to 3 independently of each other.

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In the formulas, R ³¹ to R ³⁴ are each independently methyl, isopropyl or phenyl, and R ³⁵ and R ³⁶ are each independently hydrogen, methyl, isopropyl or phenyl.

The benzimidazole derivative is a compound represented by the following formula (E-5).

≪ EMI ID =

In the formulas, Ar ¹ to Ar ³ are each independently hydrogen or aryl having 6 to 30 carbon atoms which may be substituted. Particularly preferred is anthryl benzoimidazole derivatives in which Ar ¹ may be substituted.

Specific examples of aryl having 6 to 30 carbon atoms include phenyl, 1-naphthyl, 2-naphthyl, acenaphthylene-1-yl, acenaphthylene- Yl, phenalen-1-yl, phenalen-2-yl, fluoren-3-yl, fluoren- 2-yl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, Yl, triphenylene-1-yl, triphenylene-2-yl, fluorenen-2-yl, fluorenen-2-yl, fluoranthene- Yl, chrysene-4-yl, chrysene-1-yl, chrysene-2-yl, Yl, naphthacen-2-yl, naphthacen-5-yl, perylen-1-yl, perylen- Pentacene-1-yl, pentacene-2-yl, pentacene-5-yl, pentacene-6-yl.

Specific examples of benzimidazole derivatives include 1-phenyl-2- (4- (10-phenylanthracen-9-yl) phenyl) -1H- benzo [d] imidazole, 2- (4- (10- Phenyl) -1H-benzo [d] imidazole and 2- (3- (10- (naphthalen-2-yl) anthracene- Benzo [d] imidazole, 1-phenyl-1H- benzo [d] imidazole, 5- (10- (naphthalen- Benzo [d] imidazole, 2- (4- (9,10-di (naphthalene-2-yl) Benzo [d] imidazole, 1- (4- (9,10-di (naphthalen-2-yl) anthracene- 2- yl) Benzo [d] imidazole, 5- (9,10-di (naphthalen-2-yl) anthracene- ] Imidazole.

The electron transporting layer or the electron injecting layer may further include a material capable of reducing the material for forming the electron transporting layer or the electron injecting layer. The reducing material may be various ones as long as it has a certain reducing property. For example, an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, , An oxide of a rare earth metal, a halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal, and an organic complex of a rare earth metal can be preferably used.

Preferable reducing materials include alkaline metals such as Na (work function 2.36 eV), K (copper 2.28 eV), Rb (copper 2.16 eV) or Cs (copper 1.95 eV) 2.0 to 2.5 eV) or Ba (copper eutectic 2.52 eV), and it is particularly preferable that the work function is 2.9 eV or less. Among them, the more preferable reducing material is an alkali metal of K, Rb or Cs, more preferably Rb or Cs, and most preferably Cs. These alkali metals have a particularly high reducing ability, and by the addition of a relatively small amount to a material forming the electron transporting layer or the electron injecting layer, it is possible to improve the luminescence brightness and longevity of the organic EL device. In particular, a combination of Cs and Na, Cs and K, Cs and Rb, or Cs and a combination of Cs and Na, for example, a combination of two or more alkali metals is preferable as a reducing material having a work function of 2.9 eV or less. The combination of Na and K is preferred. By including Cs, the reduction ability can be efficiently exerted. By adding to the material for forming the electron transporting layer or the electron injecting layer, it is possible to improve the luminescence brightness and longevity of the organic EL device.

≪ Negative electrode in organic electroluminescent device >

The cathode 108 serves to inject electrons into the light emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

The material for forming the cathode 108 is not particularly limited as long as electrons can be efficiently injected into the organic layer, but the same material as the material for forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium or their alloys (magnesium- Indium alloy, and aluminum-lithium alloy such as lithium fluoride / aluminum) and the like are preferable. In order to increase the electron injection efficiency and improve the device characteristics, alloys containing lithium, sodium, potassium, cesium, calcium, magnesium or their low-function metal are effective. However, these low-function metals are generally unstable in the atmosphere. In order to solve this problem, for example, a method is known in which an organic layer is doped with a small amount of lithium, cesium or magnesium to use an electrode with high stability. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide may also be used. However, the present invention is not limited thereto.

In order to protect the electrodes, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium or alloys using these metals and inorganic materials such as silica, titania and silicon nitride, polyvinyl alcohol, Based polymer compound or the like can be mentioned as a preferable example. The production method of these electrodes is not particularly limited as long as it can conduct electricity such as resistance heating, electron beam beam, sputtering, ion plating and coating.

≪ Binder agent which may be used in each layer >

The above materials used for the hole injection layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer can form each layer alone. However, as the polymer binder, polyvinyl chloride, polycarbonate, polystyrene, poly Polyvinyl pyrrolidone, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethylcellulose, vinyl acetate resin, ABS resin, Soluble resin such as a resin or a polyurethane resin or a curable resin such as a phenol resin, a xylene resin, a petroleum resin, a urea resin, a melamine resin, an unsaturated polyester resin, an alkyd resin, an epoxy resin, It is also possible.

≪ Method for producing organic electroluminescent device &

Each layer constituting the organic electroluminescence device can be formed by a method such as evaporation, resistance heating deposition, electron beam evaporation, sputtering, molecular lamination, printing, spin coating, casting, or coating Or a thin film. The film thickness of each layer thus formed is not particularly limited and may be suitably set according to the properties of the material, and is usually in the range of 2 nm to 5000 nm. The film thickness can be generally measured by a crystal oscillation type film thickness measuring apparatus or the like. In the case of thinning using a vapor deposition method, the deposition conditions differ depending on the kind of the material, the intended crystal structure of the film, the association structure, and the like. The deposition conditions are generally in the range of boat heating temperature +50 to +400 ° C, vacuum degree 10 ^-6 to 10 ^-3 Pa, deposition rate 0.01 to 50 nm / sec, substrate temperature -150 to +300 ° C, film thickness 2 nm to 5 μm As shown in Fig.

Next, as an example of a method of manufacturing an organic electroluminescent device, a method for manufacturing an organic electroluminescent device comprising an anode / a hole injecting layer / a hole transporting layer / a light emitting layer / an electron transporting layer / an electron injecting layer / a cathode made of a host material and a dopant . A thin film of a cathode material is formed on a suitable substrate by a vapor deposition method or the like to form a cathode, and then a thin film of a hole injection layer and a hole transporting layer is formed on the anode. A host material and a dopant material are co-deposited to form a thin film to form a light emitting layer, an electron transport layer and an electron injection layer are formed on the light emitting layer, and a thin film made of a material for a negative electrode is formed by evaporation or the like, An intended organic electroluminescent device can be obtained. In the fabrication of the above-described organic electroluminescent device, it is also possible to fabricate the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer and the anode in this order in reverse order.

When a direct current voltage is applied to the thus obtained organic electroluminescent device, it is sufficient to apply the positive polarity to the positive electrode and the negative polarity to the negative polarity. When a voltage of about 2 to 40 V is applied, Or cathode, and both) can be observed. Further, this organic electroluminescent element emits light even when a pulse current or an alternating current is applied. The waveform of the applied alternating current may be arbitrary.

≪ Example of application of organic electroluminescent device &

The present invention can also be applied to a display device having an organic electroluminescent device or a lighting device having an organic electroluminescent device.

The display device or the lighting device provided with the organic electroluminescent device can be manufactured by a known method such as connecting the organic electroluminescent device according to the present embodiment and a known driving device, Or the like can be appropriately used.

Examples of the display device include a panel display such as a color flat panel display and a flexible display such as a flexible color organic electroluminescence (EL) display (see, for example, JP-A-10-335066 , Japanese Unexamined Patent Application Publication No. 2003-321546, Japanese Unexamined Patent Publication No. 2004-281086, etc.). The display method of the display includes, for example, a matrix and / or a segment method. The matrix display and the segment display may coexist in the same panel.

The matrix is a matrix in which pixels for display are arranged two-dimensionally, such as a lattice image or a mosaic image, and displays a character or an image as a set of pixels. The shape and size of the pixel are determined depending on the application. For example, in the image and character display of a PC, a monitor, and a television, a quadrangular pixel with a side of 300 mu m or less is usually used. In the case of a large display such as a display panel, . In the case of monochrome display, pixels of the same color can be arranged. In the case of color display, red, green and blue pixels are displayed in a list. In this case, there are typically a delta type and a stripe type. As the driving method of the matrix, either a line-sequential driving method or an active matrix may be used. Although line-sequential driving has an advantage in that the structure is simple, when the operating characteristics are taken into consideration, there is a case where the active matrix is excellent.

In the segment method (type), a pattern is formed so as to display predetermined information, and the determined area is caused to emit light. Examples of the display include a time and temperature display in a digital clock or a thermometer, an operation status display of an audio device or an electromagnetic cooker, and a panel display of an automobile.

Examples of the illumination device include an illumination device such as an indoor illumination, and a backlight of a liquid crystal display device (see, for example, JP-A-2003-257621, JP-A-2003-277741, Japanese Unexamined Patent Publication (Kokai) No. 2004-119211). The backlight is used mainly for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a watch, an audio device, an automobile panel, a display panel, and a cover. In particular, considering that it is difficult to reduce the thickness of a liquid crystal display device, in particular, a backlight for PC applications in which thinning is a problem, since the conventional type is formed of a fluorescent lamp or a light guide plate, the backlight using the light- It is thin and lightweight.

Example

First, synthesis examples of anthracene compounds used in the examples will be described below.

≪ Synthesis Example of Compound Represented by Formula (1-1) >

≪ EMI ID =

≪ Synthesis of 9- (2,5-dichlorophenyl) -10-phenylanthracene >

(Pd (PPh ₃ ) ₂ ) was added to a solution of 15 g of 2-bromo-1,4-dichlorobenzene, 19.8 g of (10-phenylanthracen- ₄ ), 28.19 g of potassium phosphate and 260 ml of a mixed solvent of toluene and ethanol (toluene / ethanol = 4/1 (volume ratio)) were placed in a flask and stirred for 5 minutes. Then, 26 ml of water was added and the mixture was refluxed for 15 hours. After completion of the heating, the reaction solution was cooled, and 50 ml of water was added. Thereafter, the reaction mixture was extracted with toluene, dried over anhydrous sodium sulfate, and then the drying agent was removed. The solvent was distilled off under reduced pressure, and the obtained crude product was subjected to short column purification (solvent: toluene) with silica gel. Further, reprecipitation was carried out with methanol to obtain 18 g (yield: 68%) of 9- (2,5-dichlorophenyl) -10-phenylanthracene as an intermediate compound.

[Formula 97]

Synthesis of 9- ([1,1 ': 4', 1 "-terphenyl] -2'-yl) -10-

5 g of 9- (2,5-dichlorophenyl) -10-phenylanthracene as an intermediate compound, 4.55 g of phenylboronic acid, and 0.7 g of bis (dibenzylideneacetone) palladium (0) (Pd (dba) ₂ ) , 0.526 g of tricyclohexylphosphine (PCy ₃ ), 10.61 g of potassium phosphate and 50 ml of toluene were placed in a flask and stirred for 5 minutes. Then, 10 ml of water was added and the mixture was refluxed for 15 hours. After the completion of the heating, the reaction solution was cooled, water was added, and the solid portion was filtered to give the crude 1. The organic layer of the filtrate was collected, dried over anhydrous sodium sulfate, and then the drying agent was removed. The solvent was distilled off under reduced pressure to obtain the crude product 2. Next, crude product 1 and crude product 2 were combined and subjected to short column purification (solvent: toluene) with silica gel. Thereafter, the reaction product was washed with methanol and recrystallized from toluene, and further purified by sublimation to obtain 9 - ([1,1 ': 4', 1 '' - Phenyl] -2'-yl) -10-phenylanthracene (2.63 g, yield: 44%).

(98)

The structure of the compound (1-1) was confirmed by MS spectrum and NMR measurement.

The compound (1-1) had a glass transition temperature (Tg) of 97.3 캜.

[Measurement apparatus: Diamond DSC (manufactured by PERKIN-ELMER) Measuring conditions: cooling rate 200 [deg.] C / min.

Further, the glass transition temperature of the following compounds was measured under the same conditions.

≪ Synthesis Example of Compound Represented by Formula (1-301) >

[Formula 99]

<Synthesis of 9- (3,4-dichlorophenyl) -10-phenylanthracene>

(Pd (PPh ₃ ) ₂ ) was added to a solution of 15.8 g of 4-bromo-1,2-dichlorobenzene, 20.9 g of (10-phenylanthracen- ₄ ), 29.7 g of potassium phosphate and 280 ml of a mixed solvent of toluene and ethanol (toluene / ethanol = 9/1 (volume ratio)) were placed in a flask and stirred for 5 minutes. Then, 28 ml of water was added and the mixture was refluxed for 5 hours. After completion of the heating, the reaction solution was cooled, and 100 ml of water was added. Thereafter, the reaction mixture was extracted with toluene, dried over anhydrous sodium sulfate, and then the drying agent was removed. The solvent was distilled off under reduced pressure, and the obtained crude product was subjected to short column purification (solvent: toluene) with silica gel. Further, reprecipitation was carried out with methanol to obtain 12 g (yield: 43%) of 9- (3,4-dichlorophenyl) -10-phenylanthracene as an intermediate compound.

(100)

Synthesis of 9- ([1,1 ': 2', 1 "-terphenyl] -4'-yl) -10-

5 g of intermediate compound 9- (3,4-dichlorophenyl) -10-phenylanthracene, 4.55 g of phenylboronic acid, and 0.7 g of bis (dibenzylideneacetone) palladium (0) (Pd (dba) ₂ ) , 0.526 g of tricyclohexylphosphine (PCy ₃ ), 10.61 g of potassium phosphate and 50 ml of toluene were placed in a flask and stirred for 5 minutes. Then, 5 ml of water was added and the mixture was refluxed for 5 hours. After completion of the heating, the reaction solution was cooled, 50 ml of methanol was added, and the precipitate was filtered. The precipitate was further washed with methanol and water to obtain a crude product of the objective compound represented by the formula (1-301). The crude product was subjected to short column purification (solvent: toluene) using silica gel, and then recrystallized with toluene and further purified by sublimation to obtain 9 - ([1 , 1 ': 2', 1 "-terphenyl] -4'-yl) -10-phenylanthracene was obtained in a yield of 76%.

(101)

The structure of the compound (1-301) was confirmed by MS spectrum and NMR measurement.

The glass transition temperature (Tg) of the compound (1-301) was 110.1 占 폚.

<Synthesis Example of Compound Represented by Formula (1-307)> [

&Lt; EMI ID =

Synthesis of 9- (4,4 "-di (naphthalen-1-yl) - [1,1 ': 2', 1" -terphenyl] -4'-

(3.9 g) of 9- (3,4-dichlorophenyl) -10-phenylanthracene, 5.46 g of 4- (naphthalen-1-yl) phenylboronic acid, 5.46 g of bis (dibenzylideneacetone) palladium ), 0.575 g of Pd (dba) ₂ , 0.421 g of tricyclohexylphosphine (PCy ₃ ), 8.49 g of potassium phosphate and 50 ml of toluene were placed in a flask and stirred for 5 minutes. Then, 5 ml of water was added and the mixture was refluxed for 5 hours. After completion of the heating, the reaction solution was cooled, 50 ml of methanol was added, and the precipitate was filtered. The precipitate was further washed with methanol and water to obtain a crude product of the desired compound represented by the formula (1-307). The crude product was subjected to a short column purification (solvent: toluene) with silica gel, followed by recrystallization with toluene, followed by further sublimation purification to obtain the desired compound represented by the formula (1-307) 5.1 g (yield: 69.4%) of 4 "-di (naphthalen-1-yl) - [1,1 ': 2', 1" -terphenyl] -4'- yl) -10-phenylanthracene was obtained.

&Lt; EMI ID =

The structure of the compound (1-307) was confirmed by MS spectrum and NMR measurement.

The glass transition temperature (Tg) of the compound (1-307) was 147.6 占 폚.

&Lt; Synthesis Example of Compound Represented by Formula (1-3) &gt;

&Lt; EMI ID =

Synthesis of 9 - ([1,1 ': 3', 1 ": 4", 1 '": 3'", 1 "" -

Nitrogen atmosphere, intermediate compound 9 (2,5-dichloro-phenyl) -10-phenylanthracene 2 g, 3- biphenyl boronic acid 2.98 g, palladium acetate (II) (Pd (OAc) _2), 0.11 g, 2 -Dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl, 4.25 g of tripotassium phosphate and 23 ml of a mixed solvent of 1,2,4-trimethylbenzene and t-butyl alcohol (1,2,4 -Trimethylbenzene / t-butyl alcohol = 10/1 (volume ratio)) was placed in a flask and stirred for 5 minutes. Then, 3 ml of water was added and the mixture was refluxed for 8 hours. After completion of the heating, the reaction solution was cooled, water was added thereto to separate the organic layer, and the organic layer was purified by short column purification with silica gel (solvent: toluene). Thereafter, the solution was washed with methanol and recrystallized from ethyl acetate. Further, column purification (solvent: toluene / heptane = 1/3 (volume ratio)) was performed with silica gel. Finally, sublimation purification was carried out to obtain 9 - ([1,1 ': 3', 1 ": 4", 1 '": 3'", 1 " - &gt;) -2 "-yl) -10-phenylanthracene was obtained in a yield of 1.83 g (yield: 57.5%).

&Lt; EMI ID =

The structure of the compound (1-3) was confirmed by MS spectrum and NMR measurement.

The compound (1-3) had a glass transition temperature (Tg) of 104.1 占 폚.

<Synthesis Example of Compound Represented by Formula (1-23)> [

&Lt; EMI ID =

<Synthesis of 9- (5-chloro-2-methoxyphenyl) -10-phenylanthracene>

Under a nitrogen atmosphere, (5-chloro-2-methoxyphenyl) boronic acid 12.59 g, 9- bromine-10-phenylanthracene 15 g, tetrakis (triphenylphosphine) palladium _{(0) (Pd (PPh 3} ) 4 ), 19.11 g of tripotassium phosphate and 182 ml of a mixed solvent of 1,2,4-trimethylbenzene and t-butyl alcohol (1,2,4-trimethylbenzene / t-butyl alcohol = 10/1 (volume ratio)) Were placed in a flask and stirred for 5 minutes. Then, 17 ml of water was added and the mixture was refluxed for 15 hours. After completion of the heating, the reaction solution was cooled, and 100 ml of water was added. Thereafter, the solid portion was filtrated to obtain crude 1. The organic layer of the filtrate was collected, dried over anhydrous sodium sulfate, and then the drying agent was removed. The solvent was distilled off under reduced pressure to obtain the crude product 2. Thereafter, untreated products 1 and 2 were combined and subjected to short column purification (solvent: toluene) with silica gel. Further, reprecipitation was carried out with heptane to obtain 16.5 g (yield: 93%) of the intermediate compound 9- (5-chloro-2-methoxyphenyl) -10-phenylanthracene.

&Lt; EMI ID =

Synthesis of 9- (4-methoxy- [1,1 ': 3', 1 "-terphenyl] -3-yl) -10-

5 g of the intermediate compound 9- (5-chloro-2-methoxyphenyl) -10-phenylanthracene, 3.01 g of 3-biphenylboronic acid, 0.5 g of bis (dibenzylideneacetone) palladium (0) dba) ₂ ), 0.27 g of tricyclohexylphosphine (PCy ₃ ), 5.38 g of tripotassium phosphate and 50 ml of ortho-xylene were placed in a flask and stirred for 5 minutes. Then, 5 ml of water was added and the mixture was refluxed for 8 hours. After completion of the heating, the reaction solution was cooled, water was added thereto, the organic layer was separated, dried over anhydrous sodium sulfate, and then the drying agent was removed. The solvent was distilled off under reduced pressure, and the obtained solid was purified by column chromatography on silica gel (solvent: heptane / = 2/1 (volume ratio)) to give 6.3 g of the intermediate compound 9- (4-methoxy- [1,1 ': 3', 1 "-terphenyl] -3- (Yield: 97%).

(108)

Synthesis of 3- (10-phenylanthracen-9-yl) - [1,1 ': 3', 1 "-terphenyl] -4-

In a nitrogen atmosphere, 6.3 g of the intermediate compound 9- (4-methoxy- [1,1 ': 3', 1 "-terphenyl] -3- -Methyl-2-pyrrolidone was placed in a flask, and the mixture was heated at 175 DEG C for 4 hours. After completion of heating, the reaction solution was cooled, 100 mL of water was added, and the precipitate was filtered. And the obtained crude product was subjected to short column purification (solvent: toluene / ethyl acetate = 2/1 (volume ratio)) on silica gel to give the intermediate compound 3- (10-Phenylanthracene-9-yl) - [ ': 3', 1 "-terphenyl] -4-ol (6.1 g, yield: 99%).

(109)

Synthesis of 3- (10-phenylanthracen-9-yl) - [1,1 ': 3', 1 "-terphenyl] -4-yl trifluoromethanesulfonate>

6.1 g of the intermediate compound 3- (10-phenylanthracen-9-yl) - [1,1 ': 3', 1 "-terphenyl] -4-ol and 33 ml of pyridine were placed in a flask under a nitrogen atmosphere, After cooling to 0 ° C, 6.9 g of trifluoromethanesulfonic anhydride was slowly added dropwise, and then the reaction solution was stirred for 30 minutes at 0 ° C and 2 hours at room temperature. Next, water was added to the reaction solution to precipitate The obtained crude product was subjected to short column purification (solvent: toluene) with silica gel and then washed with heptane to obtain an intermediate compound 3- (10-phenylanthracene-9-yl) - [ ', 1' '- terphenyl] -4-yl trifluoromethanesulfonate (7.67 g, yield: 99%).

(110)

Synthesis of 9- ([1,1 ': 3', 1 ": 4", 1 "" -tertophenyl] -3 "

1.4 g of the intermediate compound 3- (10-phenylanthracen-9-yl) - [1,1 ': 3', 1 "-terphenyl] -4- 0.41 g, palladium acetate (II) (Pd (OAc) 2) 0.05 g, 2- dicyclohexylphosphino-2 ', 6'-methoxy-phenyl fertilization 0.14 g, tripotassium phosphate 0.94 g, 0.53 g potassium bromide and 14 ml of a mixed solvent of 1,2,4-trimethylbenzene and t-butyl alcohol (1,2,4-trimethylbenzene / t-butyl alcohol = 10/1 (volume ratio)) was added to the flask and stirred for 5 minutes. After the completion of the heating, the reaction solution was cooled, water was added thereto, the organic layer was separated, and the organic layer was purified by short column chromatography (solvent: toluene) with silica gel. Thereafter, methanol (Solvent: toluene / heptane = 1/3 (volume ratio)) was carried out using silica gel. Finally, sublimation purification was carried out using silica gel (1, 1 ': 3', 1 ": 4", 1 "" -tetraphenyl] -3 "-yl) -10-phenyl which is a target compound represented by the formula (1-23) 0.57 g (yield: 46%) of anthracene was obtained.

(111)

The structure of the compound (1-23) was confirmed by MS spectrum and NMR measurement.

The compound (1-23) had a glass transition temperature (Tg) of 102.9 占 폚.

&Lt; Synthesis Example of Compound Represented by Formula (1-53)

(112)

Synthesis of 9- (4-naphthalen-1-yl) - [1,1 ': 3', 1 "-terphenyl] -3-

3.2 g of the intermediate compound 3- (10-phenylanthracen-9-yl) - [1,1 ': 3', 1 '' - terphenyl] -4-yl trifluoromethanesulfonate, 1.31 g of boric acid, 0.11 g of palladium (II) acetate (Pd (OAc) ₂ ), 0.31 g of 2-dicyclohexylphosphino-2 ', 6'- dimethoxybiphenyl, 2.15 g of tripotassium phosphate, 1.21 g, and 24 ml of a mixed solvent of 1,2,4-trimethylbenzene and t-butyl alcohol (1,2,4-trimethylbenzene / t-butyl alcohol = 5/1 (volume ratio)) were added to the flask and stirred for 5 minutes . After completion of the heating, the reaction solution was cooled, water was added thereto, the organic layer was separated, and the organic layer was subjected to short column purification (solvent: toluene) with silica gel. Thereafter, Washed with methanol and recrystallized from ethyl acetate, and further subjected to column purification (solvent: toluene / heptane = 1/5 (volume ratio)) using silica gel. Finally, (1, 1 ': 3', 1 "-terphenyl] -3-yl) -10- To obtain 1.42 g (yield: 46%) of phenyl anthracene.

(113)

The structure of the compound (1-53) was confirmed by MS spectrum and NMR measurement.

The glass transition temperature (Tg) of the compound (1-53) was 122.8 占 폚.

&Lt; Synthesis Example of Compound Represented by Formula (1-83)

(114)

Synthesis of 9- (4-naphthalen-2-yl) - [1,1 ': 3', 1 "-terphenyl] -3-

1.4 g of the intermediate compound 3- (10-phenylanthracen-9-yl) - [1,1 ': 3', 1 "-terphenyl] -4-yl trifluoromethanesulfonate, 0.57 g of boric acid, 0.05 g of palladium (II) acetate (Pd (OAc) ₂ ), 0.14 g of 2-dicyclohexylphosphino-2 ', 6'- dimethoxybiphenyl, 0.94 g of tripotassium phosphate, g, and 14 ml of a mixed solvent of 1,2,4-trimethylbenzene and t-butyl alcohol (1,2,4-trimethylbenzene / t-butyl alcohol = 10/1 (volume ratio)) were added to the flask and stirred for 5 minutes . After completion of the heating, the reaction solution was cooled, water was added thereto, the organic layer was separated, and the organic layer was subjected to short column purification (solvent: toluene) with silica gel. Thereafter, Washed with methanol and recrystallized from ethyl acetate, and further subjected to column purification (solvent: toluene / heptane = 1/5 (volume ratio)) using silica gel. Finally, (1, 1 ': 3', 1 "-terphenyl] -3-yl) -10- 0.67 g (yield: 50%) of phenyl anthracene was obtained.

(115)

The structure of the compound (1-83) was confirmed by MS spectrum and NMR measurement.

The compound (1-83) had a glass transition temperature (Tg) of 110.2 占 폚.

<Synthesis Example of Compound Represented by Formula (1-252)> [

&Lt; EMI ID =

<Synthesis of 9- (4-methoxy- [1,1'-biphenyl] -3-yl) -10-phenylanthracene>

Nitrogen atmosphere, intermediate compound 9 (5-chloro-2-methoxyphenyl) -10-phenylanthracene 36.7 g, phenylboronic acid 17 g, ₂ bis (dibenzylideneacetone) palladium (0) (Pd (dba) ), 1.2 g of tricyclohexylphosphine (PCy ₃ ), 39.5 g of tripotassium phosphate and 400 ml of ortho xylene were placed in a flask and refluxed for 10 hours. After completion of the heating, the reaction solution was cooled, water was added thereto, the organic layer was separated, dried over anhydrous sodium sulfate, and then the drying agent was removed. The solvent was distilled off under reduced pressure, and the obtained solid was purified by column chromatography on silica gel (solvent: heptane / (Yield: 100%) as an intermediate compound 9- (4-methoxy- [1,1'-biphenyl] -3-yl) .

(117)

Synthesis of <3- (10-phenylanthracene-9-yl) - [1,1'-biphenyl]

Under a nitrogen atmosphere, 40.5 g of the intermediate compound 9- (4-methoxy- [1,1'-biphenyl] -3-yl) -10-phenylanthracene, 53.6 g of pyridine hydrochloride, 40 ml of money was placed in a flask and heated at 175 캜 for 3 hours. After completion of the heating, the reaction solution was cooled, 500 ml of water was added, and the precipitate was filtered. The precipitate was further washed with water and the resulting crude product was purified by short column purification with silica gel (solvent: toluene / ethyl acetate = 2/1 (volume ratio)) to obtain the intermediate compound 3- (10-phenylanthracene- - [1,1'-biphenyl] -4-ol (yield: 100%).

(118)

Synthesis of <3- (10-phenylanthracen-9-yl) - [1,1'-biphenyl] -4-yl trifluoromethanesulfonate>

40 g of the intermediate compound 3- (10-phenylanthracen-9-yl) - [1,1'-biphenyl] -4-ol and 450 ml of pyridine were placed in a flask, 54 g of trifluoromethanesulfonic anhydride was slowly added dropwise. Thereafter, the reaction solution was stirred at 0 占 폚 for 30 minutes and at room temperature for 2 hours. Next, water was added to the reaction solution, and the precipitate was filtered. The obtained crude product was purified by a short column purification with silica gel (solvent: toluene / heptane = 3/1 (volume ratio)) and then washed with heptane to obtain the intermediate compound 3- (10-phenylanthracene- 1,1'-biphenyl] -4-yl trifluoromethanesulfonate (yield: 93%).

(119)

Synthesis of 9- (4- (naphthalen-2-yl) - [1,1'-biphenyl] -3-yl) -10-

3 g of the intermediate compound 3- (10-phenylanthracen-9-yl) - [1,1'-biphenyl] -4-yl trifluoromethanesulfonate, 1.4 g of 2-naphthalene boronic acid, 0.12 g of palladium (II) (Pd (OAc) ₂ ), 0.33 g of 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl, 2.3 g of tripotassium phosphate, 1.29 g of potassium bromide, 26 ml of a mixed solvent of 4-trimethylbenzene and t-butyl alcohol (1,2,4-trimethylbenzene / t-butyl alcohol = 10/1 (volume ratio)) was added to the flask and stirred for 5 minutes. Then, 2 ml of water was added and the mixture was refluxed for 5 hours. After the completion of the heating, the reaction solution was cooled, water was added thereto to separate an organic layer, and the organic layer was subjected to short column purification (solvent: toluene) with silica gel. Thereafter, the solution was washed with methanol and recrystallized from ethyl acetate. Further, column purification (solvent: toluene / heptane = 1/3 (volume ratio)) was performed with silica gel. Finally, sublimation purification was carried out to obtain 9- (4- (naphthalen-2-yl) - [1,1'-biphenyl] -3-yl) -10 -Phenylanthracene (1.25 g, yield: 44%).

(120)

The structure of the compound (1-252) was confirmed by MS spectrum and NMR measurement.

The compound (1-252) had a glass transition temperature (Tg) of 107.8 캜.

&Lt; Synthesis Example of Compound Represented by Formula (1-255)

(121)

Synthesis of 9- (4 - ([1,2'-binnaphthalene] -4-yl) - [1,1'-biphenyl] -3-

3 g of the intermediate compound 3- (10-phenylanthracen-9-yl) - [1,1'-biphenyl] -4- yl trifluoromethanesulfonate and 2 - 2.5 g of 4,4,5,5-tetramethyl-1,3,2-dioxaborane, 0.04 g of palladium (II) acetate (Pd (OAc) ₂ ) 0.10 g of chlorhexylphosphino-2 ', 6'-dimethoxybiphenyl, 2.3 g of tripotassium phosphate, 1.3 g of potassium bromide and 33 ml of a mixed solvent of 1,2,4-trimethylbenzene and t-butyl alcohol (1, 2, 4-trimethylbenzene / t-butyl alcohol = 10/1 (volume ratio)) was placed in a flask and stirred for 5 minutes. Then, 3 ml of water was added and the mixture was refluxed for 15 hours. After the completion of the heating, the reaction solution was cooled, water was added thereto to separate an organic layer, and the organic layer was subjected to short column purification (solvent: toluene) with silica gel. Thereafter, the product was washed with methanol and recrystallized from ethyl acetate, and further purified by sublimation to obtain 9- (4 - ([1,2'-binnaphthalene] -4-yl) - [1,1'-biphenyl] -3-yl) -10-phenylanthracene was obtained (yield: 3%).

(122)

The structure of the compound (1-255) was confirmed by MS spectrum and NMR measurement.

The compound (1-255) had a glass transition temperature (Tg) of 150.3 占 폚.

<Synthesis Example of Compound Represented by Formula (1-261)> [

(123)

Synthesis of 9- (4- (phenanthren-9-yl) - [1,1'-biphenyl] -3-yl) -10-

3 g of the intermediate compound 3- (10-phenylanthracen-9-yl) - [1,1'-biphenyl] -4-yl trifluoromethanesulfonate, 1.8 g of 9-phenanthreneboronic acid, 0.12 g of palladium (II) acetate (Pd (OAc) ₂ ), 0.33 g of 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl, 2.3 g of tripotassium phosphate, 1.3 g of potassium bromide, , And 26 ml of a mixed solvent of 4-trimethylbenzene and t-butyl alcohol (1,2,4-trimethylbenzene / t-butyl alcohol = 10/1 (volume ratio)) were placed in a flask and stirred for 5 minutes. Then, 2 ml of water was added and the mixture was refluxed for 6 hours. After the completion of the heating, the reaction solution was cooled, water was added thereto to separate an organic layer, and the organic layer was subjected to short column purification (solvent: toluene) with silica gel. Thereafter, the solution was washed with methanol and recrystallized from ethyl acetate. Further, column purification (solvent: toluene / heptane = 1/3 (volume ratio)) was performed with silica gel. Finally, sublimation purification was carried out to obtain 9- (4- (phenanthren-9-yl) - [1,1'-biphenyl] -3-yl) - 0.57 g (yield: 18%) of 10-phenylanthracene was obtained.

(124)

The structure of the compound (1-261) was confirmed by MS spectrum and NMR measurement.

The glass transition temperature (Tg) of the compound (1-261) was 136.0 占 폚.

<Synthesis Example of Compound Represented by Formula (1-262)> [

(125)

Synthesis of 9- (4- (triphenylene-2-yl) - [1,1'-biphenyl] -3-yl)

3 g of the intermediate compound 3- (10-phenylanthracen-9-yl) - [1,1'-biphenyl] -4-yl trifluoromethanesulfonate, 1.8 g of 2-triphenyleneboronic acid, 0.04 g of palladium (II) acetate (Pd (OAc) ₂ ), 0.10 g of 2-dicyclohexylphosphino-2 ', 6'- dimethoxybiphenyl, 2.3 g of tripotassium phosphate, 1.3 g of potassium bromide and 1, , And 33 ml of a mixed solvent of 4-trimethylbenzene and t-butyl alcohol (1,2,4-trimethylbenzene / t-butyl alcohol = 10/1 (volume ratio)) were placed in a flask and stirred for 5 minutes. Then, 3 ml of water was added, and the mixture was refluxed for 28 hours. After the completion of the heating, the reaction solution was cooled, water was added thereto to separate an organic layer, and the organic layer was subjected to short column purification (solvent: toluene) with silica gel. Thereafter, the reaction mixture was washed with methanol and recrystallized from ethyl acetate, and further purified by sublimation to obtain 9- (4- (triphenylene-2-yl) - [1,1'-biphenyl] -3-yl) -10-phenylanthracene (0.75 g, yield: 22%).

(126)

The structure of the compound (1-262) was confirmed by MS spectrum and NMR measurement.

The compound (1-262) had a glass transition temperature (Tg) of 148.4 캜.

&Lt; Synthesis Example of Compound Represented by Formula (1-283)

(127)

1 '': 3 '', 1 '' '- phenylphenyl] -2''- -10-phenylanthracene &gt;

2 g of the intermediate compound 9- (2,5-dichlorophenyl) -10-phenylanthracene, 4.12 g of [1,1 ': 3', 1 "-ter] -5'- 0.11 g of palladium (II) acetate (II) (Pd (OAc) ₂ ), 0.31 g of 2-dicyclohexylphosphino-2 ', 6'- dimethoxybiphenyl, 4.25 g of tripotassium phosphate and 1,2,4- (1,2,4-trimethylbenzene / t-butyl alcohol = 10/1 (volume ratio)) was added to the flask, and the mixture was stirred for 5 minutes. Then, 3 ml of water was added After the completion of the heating, the reaction solution was cooled, water was added thereto, and the organic layer was separated, and the organic layer was purified by short column purification (solvent: toluene) with silica gel, then reprecipitated with methanol, The column was subjected to sublimation purification to obtain a target compound represented by the formula (1-283), 9- (5 ', 5', 5'-tetramethyldisiloxane) "- 1.90 g (yield: 48%) of phenyl- [1,1 ': 3', 1 ": 4", 1 '": 3'", 1 " %).

(128)

The structure of the compound (1-283) was confirmed by MS spectrum and NMR measurement.

The compound (1-283) had a glass transition temperature (Tg) of 145.3 占 폚.

<Synthesis Example of Compound Represented by Formula (1-559)> [

&Lt; EMI ID =

Synthesis of <2-chloro-4- (10-phenylanthracen-9-yl) phenol>

Under nitrogen atmosphere, 4-Brom-2-chlorophenol 9 g, (10- phenyl-anthracene-9-yl) boronic acid 12.93 g, bis (dibenzylideneacetone) palladium (0) (Pd (dba) 2) 0.75 g , 0.55 g of tricyclohexylphosphine (PCy ₃ ), 18.42 g of tripotassium phosphate and 180 ml of a mixed solvent of toluene and ethanol (toluene / ethanol = 4/1 (volume ratio)) were placed in a flask and stirred for 5 minutes. Then, 18 ml of water was added and the mixture was refluxed for 15 hours. After completion of the heating, the reaction solution was cooled, and 100 ml of water was added. Thereafter, the reaction mixture was extracted with toluene and dried over anhydrous sodium sulfate. The drying agent was removed, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by column chromatography on silica gel (solvent: heptane / toluene = ) To obtain 8.3 g (yield: 50%) of the intermediate compound 2-chloro-4- (10-phenylanthracen-9-yl) phenol.

(130)

Synthesis of 5- (10-phenylanthracen-9-yl) - [1,1'-biphenyl] -2-

7.9 g of the intermediate compound 2-chloro-4- (10-phenylanthracene-9-yl) phenol, 3.79 g of phenylboronic acid, and 0.5 g of bis (dibenzylideneacetone) palladium (0) (Pd (dba) ₂ ) , 0.44 g of tricyclohexylphosphine (PCy ₃ ), 8.81 g of tripotassium phosphate and 80 ml of ortho-xylene were placed in a flask and stirred for 5 minutes. Then, 8 ml of water was added and the mixture was refluxed for 5 hours. After the completion of the heating, the reaction solution was cooled and water was added. Thereafter, the solid portion was filtrated to obtain crude 1. The organic layer of the filtrate was collected, dried over anhydrous sodium sulfate, and then the drying agent was removed. The solvent was distilled off under reduced pressure to obtain the crude product 2. Thereafter, untreated products 1 and 2 were combined and subjected to short column purification (solvent: toluene) with silica gel. Further, reprecipitation was carried out with heptane to obtain 8.4 g (yield: 95.9%) of intermediate compound 5- (10-phenylanthracen-9-yl) - [1,1'- biphenyl] -2-

[Formula 131]

<Synthesis of 5- (10-phenylanthracen-9-yl) - [1,1'-biphenyl] -2-yl trifluoromethanesulfonate>

8.4 g of the intermediate compound 5- (10-phenylanthracen-9-yl) - [1,1'-biphenyl] -2-ol and 80 ml of pyridine were placed in a flask, cooled to 0 ° C, 11.2 g of trifluoromethanesulfonic anhydride was slowly added dropwise. Thereafter, the reaction solution was stirred at 0 占 폚 for 30 minutes and at room temperature for 2 hours. Next, water was added to the reaction solution, and the precipitate was filtered. The obtained crude product was subjected to short column purification (solvent: toluene) with silica gel and then washed with heptane to obtain Intermediate Compound 5- (10-Phenylanthracene-9-yl) - [ To obtain 11 g (yield: 100%) of 2-yl trifluoromethanesulfonate.

(132)

Synthesis of 9- (6- (naphthalen-1-yl) - [1,1'-biphenyl] -3-yl) -10-

2.6 g of the intermediate compound 5- (10-phenylanthracen-9-yl) - [1,1'-biphenyl] -2-yl trifluoromethanesulfonate, 1.21 g of 1-naphthalene boronic acid, 0.11 g of palladium (II) (Pd (OAc) ₂ ), 0.29 g of 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl, 1.99 g of tripotassium phosphate, 1.12 g of potassium bromide, 20 ml of a mixed solvent of 4-trimethylbenzene and t-butyl alcohol (1,2,4-trimethylbenzene / t-butyl alcohol = 10/1 (volume ratio)) was added to the flask and stirred for 5 minutes. Then, 2 ml of water was added and the mixture was refluxed for 6 hours. After the completion of the heating, the reaction solution was cooled, water was added thereto to separate an organic layer, and the organic layer was subjected to short column purification (solvent: toluene) with silica gel. Thereafter, the solution was washed with methanol and recrystallized from ethyl acetate. Further, column purification (solvent: toluene / heptane = 1/3 (volume ratio)) was performed with silica gel. Finally, sublimation purification was carried out to obtain 9- (6- (naphthalen-1-yl) - [1,1'-biphenyl] -3-yl) -10 -Phenylanthracene (1.2 g, yield: 48%).

(133)

The structure of the compound (1-559) was confirmed by MS spectrum and NMR measurement.

The glass transition temperature (Tg) of the compound (1-559) was 126.6 占 폚.

<Synthesis Example of Compound Represented by Formula (1-560)> [

(134)

Synthesis of 9- (6- (naphthalen-2-yl) - [1,1'-biphenyl] -3-yl)

2.6 g of the intermediate compound 5- (10-phenylanthracen-9-yl) - [1,1'-biphenyl] -2-yl trifluoromethanesulfonate, 1.21 g of 2-naphthalene boronic acid, 0.11 g of palladium (II) (Pd (OAc) ₂ ), 0.29 g of 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl, 1.99 g of tripotassium phosphate, 1.12 g of potassium bromide, 20 ml of a mixed solvent of 4-trimethylbenzene and t-butyl alcohol (1,2,4-trimethylbenzene / t-butyl alcohol = 10/1 (volume ratio)) was added to the flask and stirred for 5 minutes. Then, 2 ml of water was added and the mixture was refluxed for 6 hours. After the completion of the heating, the reaction solution was cooled, water was added thereto to separate an organic layer, and the organic layer was subjected to short column purification (solvent: toluene) with silica gel. Thereafter, the solution was washed with methanol and recrystallized from ethyl acetate. Further, column purification (solvent: toluene / heptane = 1/3 (volume ratio)) was performed with silica gel. Finally, sublimation purification is carried out to obtain 9- (6- (naphthalen-2-yl) - [1,1'-biphenyl] -3-yl) -10 -Phenylanthracene (yield: 56%).

(135)

The structure of the compound (1-560) was confirmed by MS spectrum and NMR measurement.

The compound (1-560) had a glass transition temperature (Tg) of 116.6 ° C.

&Lt; Synthesis Example of Compound Represented by Formula (2-1)

&Lt; EMI ID =

Synthesis of 9- (2-methoxy-5 (naphthalen-1-yl) phenyl) -10-

In a nitrogen atmosphere, 6 g of the intermediate compound 9- (5-chloro-2-methoxyphenyl) -10-phenylanthracene, 3.14 g of 1-naphthaleneboronic acid, 0.5 g of bis (dibenzylideneacetone) palladium (0) ) ₂ ), 0.19 g of tricyclohexylphosphine (PCy ₃ ), 6.45 g of tripotassium phosphate and 50 ml of xylene were placed in a flask and stirred for 5 minutes. Then, 5 ml of water was added and the mixture was refluxed for 14 hours. After completion of the heating, the reaction solution was cooled, water was added thereto, the organic layer was separated, dried over anhydrous sodium sulfate, and then the drying agent was removed. The solvent was distilled off under reduced pressure, and the obtained solid was purified by column chromatography on silica gel (solvent: heptane / = 2/1 (volume ratio)) to obtain 5.3 g (yield: 71.7%) of intermediate compound 9- (2-methoxy-5 (naphthalen-1-yl) phenyl) -10-phenylanthracene.

(137)

Synthesis of 4- (naphthalen-1-yl) -2- (10-phenylanthracene-9-yl)

5.3 g of the intermediate compound 9- (2-methoxy-5 (naphthalen-1-yl) phenyl) -10-phenylanthracene, 6.3 g of pyridine hydrochloride and 5 ml of 1-methyl- And the mixture was heated at 175 캜 for 4 hours. After completion of the heating, the reaction solution was cooled, 100 ml of water was added, and the precipitate was filtered. The precipitate was further washed with water and the obtained crude product was purified by short column purification with silica gel (solvent: toluene / ethyl acetate = 2/1 (volume ratio)) to obtain an intermediate compound 4- (naphthalen- (10-phenylanthracen-9-yl) phenol (yield: 89%).

&Lt; EMI ID =

<Synthesis of 4- (naphthalen-1-yl) -2- (10-phenylanthracen-9-yl) phenyltrifluoromethanesulfonate>

4.6 g of the intermediate compound 4- (naphthalen-1-yl) -2- (10-phenylanthracen-9-yl) phenol and 25 ml of pyridine were placed in a flask, cooled to 0 ° C, 5.5 g of methanesulfonic anhydride was slowly added dropwise. Thereafter, the reaction solution was stirred at 0 占 폚 for 30 minutes and at room temperature for 2 hours. Next, water was added to the reaction solution, and the precipitate was filtered. The resulting crude product was subjected to short column purification (solvent: toluene) with silica gel and then washed with heptane to obtain the intermediate compound 4- (naphthalene-1-yl) -2- (10- 5.95 g (yield: 100%) of trifluoromethanesulfonate was obtained.

[Chemical Formula 139]

Synthesis of 9- (4- (naphthalen-1-yl) - ([1,1'-biphenyl] -2-yl)

4.7 g of the intermediate compound 4- (naphthalen-1-yl) -2- (10-phenylanthracene-9-yl) phenyltrifluoromethanesulfonate, 1.42 g of phenylboronic acid, , 0.09 g of Pd (OAc) ₂ ), 0.27 g of 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl, 1.65 g of tripotassium phosphate, 0.80 g of sodium bromide, and 1,2,4-trimethylbenzene 33 Ml were placed in a flask and stirred for 5 minutes. Then, 3 ml of water was added and the mixture was refluxed for 8 hours. After the completion of the heating, the reaction solution was cooled, water was added thereto to separate an organic layer, and the organic layer was subjected to short column purification (solvent: toluene) with silica gel. Thereafter, reprecipitation was performed with methanol, and column purification (solvent: toluene / heptane = 1/6 (volume ratio)) was further performed with silica gel. Finally, sublimation purification was carried out to obtain 9- (4- (naphthalen-1-yl) - ([1,1'-biphenyl] -2-yl) To obtain 1.68 g (yield: 40.5%) of 10-phenylanthracene.

&Lt; EMI ID =

The structure of the compound (2-1) was confirmed by MS spectrum and NMR measurement.

The compound (2-1) had a glass transition temperature (Tg) of 106.4 占 폚.

&Lt; Synthesis Example of Comparative Example Compound (A) &gt;

(141)

Synthesis of 9 - ([1,1 ': 3', 1 "-terphenyl] -5'-yl) -10-

Under a nitrogen atmosphere, 3, 5-diphenyl benzene bromine 3.87 g, (10- phenyl-anthracene-9-yl) boronic acid 4.1 g, tetrakis (triphenylphosphine) palladium _{(0) (Pd (PPh 3} ) 4) , 5.31 g of potassium phosphate and 50 ml of a mixed solvent of toluene and ethanol (toluene / ethanol = 3/1 (volume ratio)) were placed in a flask and stirred for 5 minutes. Then, 5 ml of water was added and the mixture was refluxed for 7 hours. After completion of the heating, the reaction solution was cooled, and 50 ml of water was added. Thereafter, the reaction mixture was extracted with toluene, dried over anhydrous sodium sulfate, and then the drying agent was removed. The solvent was distilled off under reduced pressure, and the obtained crude product was subjected to short column purification (solvent: toluene) with silica gel. ([1,1 ': 3', 1 "-terphenyl] -5'-yl) -10 &lt; / RTI &gt; (Yield: 54.7%) was obtained in the same manner as in Reference Example 1. Further, the compound (A) of Comparative Example is Compound E87 in which the synthesis example is described in Patent Document 1 (Japanese Unexamined Patent Application Publication No. 2000-273056).

(142)

The structure of Comparative Example Compound (A) was confirmed by MS spectrum and NMR measurement.

The glass transition temperature (Tg) of Comparative Example Compound (A) was 104.9 占 폚.

&Lt; Synthesis Example of Comparative Example Compound (B) &gt;

(143)

<Synthesis of 9 - ([1,1'-biphenyl] -2-yl) -10-phenylanthracene>

In a nitrogen atmosphere, 3 g of 9-bromo-10-anthracene, 2.14 g of 2-biphenylboronic acid, 0.16 g of bis (dibenzylideneacetone) palladium (0) (Pd (dba) ₂ ) (PCy ₃ ), 3.82 g of tripotassium phosphate and 36 ml of a mixed solvent of 1,2,4-trimethylbenzene and t-butyl alcohol (1,2,4-trimethylbenzene / t-butyl alcohol = 10/1 Capacity ratio)) was placed in a flask and stirred for 5 minutes. Then, 3 ml of water was added and the mixture was refluxed for 8 hours. After completion of the heating, the reaction solution was cooled, water was added thereto to separate the organic layer, and the organic layer was purified by short column purification with silica gel (solvent: toluene). Thereafter, reprecipitation was performed with methanol, and further recrystallization was performed with ethyl acetate. Finally, sublimation purification was conducted to obtain 1.99 g (yield: 54%) of 9 - ([1,1'-biphenyl] -2-yl) -10-phenylanthracene as a comparative compound (B) .

(144)

The structure of Comparative Example Compound (B) was confirmed by MS spectrum and NMR measurement.

The glass transition temperature (Tg) of the comparative compound (B) was 65.1 占 폚.

&Lt; Evaluation of organic EL device &gt;

Hereinafter, to describe the present invention in more detail, examples of the organic EL device using the compound of the present invention are shown, but the present invention is not limited thereto.

(V), EL emission wavelength (nm), and external quantum efficiency (%), which are the characteristics at the time of light emission of 1000 cd / m 2, were measured for each of the organic EL devices according to Examples 1 and 2 and Comparative Example 1 (Time) in which the luminance was maintained at 90% (1800 cd / m &lt; 2 &gt;) or more of the initial luminance when a constant current was driven at a current density of 2000 cd / Examples and Comparative Examples are described below in detail.

The quantum efficiency of the light emitting device is the internal quantum efficiency and the external quantum efficiency. The internal quantum efficiency represents the rate at which the external energy injected as electrons (or holes) into the light emitting layer of the light emitting device is converted purely into photons. On the other hand, it is the external quantum efficiency that this photon is calculated on the basis of the amount emitted to the outside of the light emitting element, and a part of the photon generated in the light emitting layer is absorbed or continuously reflected inside the light emitting element, , The external quantum efficiency is lower than the internal quantum efficiency.

The method of measuring the external quantum efficiency is as follows. Using a voltage / current generator R6144 manufactured by the company of Advantest, a voltage of 1000 cd / m &lt; 2 &gt; The spectral radiance of the visible light region was measured from the vertical direction with respect to the light emitting surface using the spectro radiance luminance meter SR-3AR manufactured by TOPCON. The value obtained by dividing the value of the spectral radiance of each wavelength component of the measured wavelength component by the wavelength energy and multiplying by? Is the photon number at each wavelength, assuming that the light emitting surface is a complete diffusing surface. Then, the number of photons was integrated into the entire wavelength range observed, and the total number of photons emitted from the device was obtained. The numerical value obtained by dividing the total number of photons emitted from the device by the number of carriers injected into the device is the external quantum efficiency.

Table 1 shows the material composition of each layer in the organic EL device according to Example 1, Example 2, and Comparative Example 1 produced.

In Table 1, &quot; HI &quot; represents N ⁴ , N ^{4 '} -diphenyl-N ⁴ , N ^4' -bis (9-phenyl-9H-carbazol- ] -4,4'-diamine, "NPD" is N, N'-diphenyl-N, N'-dinaphthyl-4,4'-diaminobiphenyl, "BD1" -N ^5, N ⁹ - diphenyl -N ^5, N ⁹ - bis (4- (trimethylsilanyl) phenyl) -7H- benzo [c] fluorene -5,9- diamine, "ET1" is 4,4 '- ((2-phenylanthracene-9,10-diyl) bis (4,1-phenylene)) dipyridine. And &quot; Liq &quot; is 8-quinolinol lithium. The chemical structure is shown below.

(145)

&Lt; Example 1 &gt;

&Lt; Device using Compound (1-1) as the host material of the light emitting layer &gt;

A glass substrate (manufactured by Optoscience Co., Ltd.) having a size of 26 mm x 28 mm x 0.7 mm, in which ITO film having a thickness of 180 nm was polished to 150 nm by sputtering, was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and molybdenum-containing boats with HI, molybdenum vapor deposition boat with NPD, 1) molybdenum booster boat with BD1, molybdenum booster boat with BD1, molybdenum boats with ET1, molybdenum boats with Liq, molybdenum boats with magnesium and molybdenum with silver I was wearing my boots.

The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum tank was evacuated to 5 x 10 &lt; ~ ⁴ &gt; Pa. First, an evacuation boat containing HI was heated to form a hole injecting layer with a film thickness of 40 nm. Subsequently, the evacuation boat containing NPD was heated And a film thickness of 30 nm was deposited thereon to form a hole transport layer. Next, the vapor deposition boat containing the compound (1-1) and the vapor deposition boat containing the BD1 were simultaneously heated to deposit a film having a thickness of 35 nm to form a light emitting layer. The deposition rate was controlled so that the weight ratio of compound (1-1) and BD1 was approximately 95: 5. Next, an evaporation boat containing ET1 was heated to deposit a film having a thickness of 15 nm to form an electron transport layer. The deposition rate of each layer was 0.01 to 1 nm / sec.

Thereafter, the deposition boats containing Liq were heated to deposit at a deposition rate of 0.01 to 0.1 nm / sec so as to have a film thickness of 1 nm. Subsequently, a boat containing magnesium and a boat containing silver were simultaneously heated to deposit a film having a thickness of 100 nm to form a negative electrode. At this time, the deposition rate was controlled so that the ratio of atomic ratio of magnesium and silver was 10: 1, and the deposition rate was set to 0.01 to 2 nm / sec to obtain an organic EL device.

When the characteristics at the time of light emission of 1000 cd / m 2 were measured using the ITO electrode as a positive electrode and Liq / magnesium + silver electrode as a negative electrode, the driving voltage was 5.87 V and the external quantum efficiency was 5.85% (blue light emission with a wavelength of about 459 nm) . The constant current driving test was carried out with the current density for obtaining the initial luminance of 2000 cd / m &lt; 2 &gt;, and the time for maintaining the luminance of 90% (1800 cd / m &lt; 2 &gt;

&Lt; Example 2 &gt;

&Lt; Device using Compound (1-301) as the host material of the light emitting layer &gt;

An organic EL device was obtained in the same manner as in Example 1 except that the compound (1-1) as the host material of the light emitting layer was changed to the compound (1-301). When the characteristics at the time of light emission of 1000 cd / m 2 were measured using the ITO electrode as a positive electrode and Liq / magnesium + silver electrode as a negative electrode, the driving voltage was 5.78 V and the external quantum efficiency was 5.70% (blue light emission with a wavelength of about 459 nm) . As a result of conducting a constant current drive test with a current density for obtaining an initial luminance of 2000 cd / m &lt; 2 &gt;, the time for maintaining the luminance of 90% (1800 cd / m &lt; 2 &gt;

&Lt; Comparative Example 1 &

An organic EL device was obtained in the same manner as in Example 1 except that the compound (1-1), which is the host material of the light emitting layer, was changed to the compound (A). When the characteristics at the time of light emission of 1000 cd / m2 were measured using the ITO electrode as a positive electrode and Liq / magnesium + silver electrode as a negative electrode, the driving voltage was 6.35 V and the external quantum efficiency was 5.02% (blue light emission with a wavelength of about 464 nm) . The constant current driving test was carried out by the current density for obtaining the initial luminance of 2000 cd / m 2, and as a result, the time for maintaining the luminance of 90% (1800 cd / m 2) or more of the initial value was 10 hours.

Table 2 summarizes the above results.

Table 3 shows the material composition of each layer in the organic EL devices according to Examples 3 to 10, Comparative Example 2 and Comparative Example 3 thus produced.

In Table 3, &quot; HI2 &quot; is 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile. The chemical structure is shown below.

(146)

&Lt; Example 3 &gt;

&Lt; Device using Compound (1-1) as the host material of the light emitting layer &gt;

A glass substrate (manufactured by Optoscience Co., Ltd.) having a size of 26 mm x 28 mm x 0.7 mm, in which ITO film having a thickness of 180 nm was polished to 150 nm by sputtering, was used as a transparent support substrate. The transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and molybdenum vapor deposition boat containing HI, molybdenum vapor deposition boat containing HI 2, and molybdenum vapor deposition vessel containing NPD Boats, molybdenum boats with compound (1-1) of the present invention, molybdenum boats with BD1, molybdenum boats with ET1, molybdenum boats with Liq, molybdenum with magnesium And boats fitted with molybdenum boats fitted with silver.

The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum tank was evacuated to 5 x 10 &lt; ^-4 &gt; Pa. First, an evacuation boat containing HI was heated to deposit a film having a thickness of 40 nm to form a first hole injection layer. Followed by evaporation to a film thickness of 5 nm to form a second hole injection layer. Next, an evaporation donor boat containing NPD was heated to deposit a film having a thickness of 20 nm to form a hole transport layer. Next, the vapor deposition boat containing the compound (1-1) and the vapor deposition boat containing the BD1 were simultaneously heated to deposit a film having a thickness of 25 nm to form a light emitting layer. The deposition rate was controlled so that the weight ratio of compound (1-1) and BD1 was approximately 95: 5. Next, an evaporation boat containing ET1 was heated to deposit a film having a thickness of 15 nm to form an electron transport layer. The deposition rate of each layer was 0.01 to 1 nm / sec.

Thereafter, the deposition boats containing Liq were heated to deposit at a deposition rate of 0.01 to 0.1 nm / sec so as to have a film thickness of 1 nm. Subsequently, a boat containing magnesium and a boat containing silver were simultaneously heated to deposit a film having a thickness of 100 nm to form a negative electrode. At this time, the deposition rate was adjusted so that the ratio of atomic ratio of magnesium to silver was 10: 1, and the deposition rate was set to 0.01 to 2 nm / sec to obtain an organic EL device.

When the characteristics at the time of light emission of 1000 cd / m2 were measured using the ITO electrode as a positive electrode and Liq / magnesium + silver electrode as a negative electrode, the driving voltage was 4.34 V and the external quantum efficiency was 5.08% (blue light emission with a wavelength of about 457 nm) . As a result of the constant current driving test using the current density for obtaining the initial luminance of 2000 cd / m 2, the time for maintaining the luminance of 90% (1800 cd / m 2) or more of the initial value was 198 hours.

<Example 4>

&Lt; Device using Compound (1-3) as the host material of the light emitting layer &gt;

An organic EL device was obtained in the same manner as in Example 3 except that the compound (1-1), which is the host material of the light emitting layer, was changed to the compound (1-3). When the characteristics at the time of light emission of 1000 cd / m 2 were measured using the ITO electrode as a positive electrode and Liq / magnesium + silver electrode as a negative electrode, the driving voltage was 4.39 V and the external quantum efficiency was 4.85% (blue light emission with a wavelength of about 457 nm) . As a result of conducting a constant current driving test with a current density for obtaining an initial luminance of 2000 cd / m 2, the time for maintaining the luminance of 90% (1800 cd / m 2) or more of the initial value was 140 hours.

&Lt; Example 5 &gt;

&Lt; Device using Compound (1-23) as a host material in a light emitting layer &gt;

An organic EL device was obtained in the same manner as in Example 3 except that the compound (1-1), which is the host material of the light emitting layer, was changed to the compound (1-23). When the characteristics at the time of light emission of 1000 cd / ㎡ were measured using the ITO electrode as a positive electrode and Liq / magnesium + silver electrode as a negative electrode, the driving voltage was 4.31 V and the external quantum efficiency was 4.57% (blue light emission with a wavelength of about 455 nm) . As a result of conducting a constant current driving test with a current density for obtaining an initial luminance of 2000 cd / m 2, the time for maintaining the luminance of 90% (1800 cd / m 2) or more of the initial value was 135 hours.

&Lt; Example 6 &gt;

&Lt; Device using Compound (1-53) as a host material in the light emitting layer &gt;

An organic EL device was obtained in the same manner as in Example 3 except that the compound (1-1), which is the host material of the light emitting layer, was changed to the compound (1-53). When the characteristics at the time of light emission of 1000 cd / m2 were measured using the ITO electrode as a positive electrode and Liq / magnesium + silver electrode as a negative electrode, the driving voltage was 4.52 V and the external quantum efficiency was 4.80% (blue light emission with a wavelength of about 457 nm) . As a result of carrying out the constant current driving test by the current density for obtaining the initial luminance of 2000 cd / m &lt; 2 &gt;, the time for maintaining the luminance of 90% (1800 cd / m &lt; 2 &gt;

&Lt; Example 7 &gt;

&Lt; Device using Compound (1-83) as a host material in the light emitting layer &gt;

An organic EL device was obtained in the same manner as in Example 3 except that the compound (1-1) as the host material of the light emitting layer was changed to the compound (1-83). When the characteristics at the time of light emission of 1000 cd / m 2 were measured using the ITO electrode as a positive electrode and Liq / magnesium + silver electrode as a cathode, the driving voltage was 4.16 V and the external quantum efficiency was 4.62% (blue light emission with a wavelength of about 456 nm) . The constant current driving test was carried out by the current density for obtaining the initial luminance of 2000 cd / m 2, and as a result, the time for maintaining the luminance of 90% (1800 cd / m 2) or more of the initial value was 97 hours.

&Lt; Example 8 &gt;

&Lt; Device using Compound (1-261) as a host material in a light emitting layer &gt;

An organic EL device was obtained in the same manner as in Example 3 except that the compound (1-1) as the host material of the light emitting layer was changed to the compound (1-261). When the characteristics at the time of light emission of 1000 cd / m 2 were measured using the ITO electrode as a positive electrode and Liq / magnesium + silver electrode as a negative electrode, the driving voltage was 4.43 V and the external quantum efficiency was 4.91% (blue light emission with a wavelength of about 457 nm) . Further, as a result of carrying out a constant current driving test with a current density for obtaining an initial luminance of 2000 cd / m 2, the time for maintaining the luminance of 90% (1800 cd / m 2) or more of the initial value was 83 hours.

&Lt; Example 9 &gt;

&Lt; Device using Compound (1-262) as a host material in the light emitting layer &gt;

An organic EL device was obtained in the same manner as in Example 3 except that the compound (1-1) as the host material of the light emitting layer was changed to the compound (1-262). When the characteristics at the time of light emission of 1000 cd / m2 were measured using the ITO electrode as a positive electrode and Liq / magnesium + silver electrode as a negative electrode, the driving voltage was 3.82 V and the external quantum efficiency was 4.94% (blue light emission with a wavelength of about 459 nm) . As a result of the constant current drive test using the current density for obtaining the initial luminance of 2000 cd / m 2, the time to maintain the luminance of 90% (1800 cd / m 2) or more of the initial value was 68 hours.

&Lt; Example 10 &gt;

&Lt; Device using Compound (2-1) as the host material of the light emitting layer &gt;

An organic EL device was obtained in the same manner as in Example 3 except that the compound (1-1), which is the host material of the light emitting layer, was changed to the compound (2-1). When the characteristics at the time of light emission of 1000 cd / m 2 were measured using the ITO electrode as a positive electrode and Liq / magnesium + silver electrode as a negative electrode, the driving voltage was 4.24 V and the external quantum efficiency was 4.92% (blue light emission with a wavelength of about 456 nm) . As a result of carrying out the constant current driving test by the current density for obtaining the initial luminance of 2000 cd / m 2, the time for maintaining the luminance of 90% (1800 cd / m 2) or more of the initial value was 171 hours.

&Lt; Comparative Example 2 &

An organic EL device was obtained in the same manner as in Example 3 except that the compound (1-1), which is the host material of the light emitting layer, was changed to the compound (A). When the characteristics at the time of light emission of 1000 cd / m 2 were measured using the ITO electrode as a positive electrode and Liq / magnesium + silver electrode as a negative electrode, the driving voltage was 4.55 V and the external quantum efficiency was 4.14% (blue light emission with a wavelength of about 456 nm) . As a result of conducting a constant current driving test with a current density for obtaining an initial luminance of 2000 cd / m 2, the time for maintaining the luminance of 90% (1800 cd / m 2) or more of the initial value was 6 hours.

&Lt; Comparative Example 3 &

An organic EL device was obtained in the same manner as in Example 3 except that the compound (1-1) as the host material of the light emitting layer was changed to the compound (B). When the characteristics at the time of light emission of 1000 cd / m 2 were measured using the ITO electrode as a positive electrode and Liq / magnesium + silver electrode as a cathode, the driving voltage was 4.56 V and the external quantum efficiency was 4.74% (blue light emission with a wavelength of about 455 nm) . The constant current driving test was carried out by the current density for obtaining the initial luminance of 2000 cd / m 2, and as a result, it was 28 hours that the luminance was maintained at 90% (1800 cd / m 2) or more of the initial value.

Table 4 summarizes the above results.

Industrial availability

According to a preferred embodiment of the present invention, it is possible to provide an organic electroluminescent device excellent in driving voltage, luminous efficiency, and device life, a display device having the same, and a lighting device including the same.

100; Organic electroluminescent device
101; Board
102; anode
103; Hole injection layer
104; Hole transport layer
105; The light-
106; Electron transport layer
107; Electron injection layer
108; cathode

Claims (23)

A light emitting layer material comprising an anthracene compound represented by the following general formula (1).

In the formula (1)
Ar is an aryl having 6 to 18 carbon atoms, which may be substituted with aryl having 6 to 18 carbon atoms, n is 1 or 2, and when n is 1, Ar is bonded to the x position, and when n is 2 Ar is bonded to both the x position and the y position,
Ar ¹ is an aryl having 6 to 18 carbon atoms, which may be substituted with aryl having 6 to 18 carbon atoms, m is an integer from 0 to 2, m has a structure of Ar ¹ when m is 2,
R is independently an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 3 to 6 carbon atoms, a is an integer of 0 to 2, b is 0 or 1, c is an integer of 0 to 2, and d is 0 Is an integer of 2 to 2,
At least one hydrogen in the anthracene compound represented by the formula (1) may be substituted with deuterium. The method according to claim 1,
Ar is phenyl, naphthyl, phenanthryl or triphenylenyl, which may be substituted with phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl, n is 1 or 2, and when n is 1 Ar is bonded to the x position, and when n is 2, Ar is bonded to both the x position and the y position,
Ar ¹ is phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl, which may be substituted by phenyl, naphthyl or phenanthryl, m is an integer of 0 to 2,
Wherein R is independently methyl, ethyl, n-propyl, isopropyl, t-butyl or cyclohexyl, a is 0 or 1, b is 0 or 1, c is 0 and d is 0 material. 3. The method according to claim 1 or 2,
n is 1, and Ar is bonded to the x-position. The method according to claim 1,
Wherein the anthracene compound represented by the general formula (1) is a compound having the following structure.

A material for a light-emitting layer containing an anthracene compound represented by the following general formula (2).

The naphthalene ring represented by the formula (2) is a 1-naphthyl group or a 2-naphthyl group which is bonded to a phenyl group,
Ar is phenyl, which may be substituted with phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl,
Ar ¹ is an aryl having 6 to 18 carbon atoms, which may be substituted with aryl having 6 to 18 carbon atoms, m is an integer from 0 to 2, and when m is 2, the structure of Ar ¹ is the same,
R is independently an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 3 to 6 carbon atoms, a is an integer of 0 to 2, b is 0 or 1, c is an integer of 0 to 2, and d is 0 Is an integer of 2 to 2,
At least one hydrogen in the anthracene compound represented by the formula (2) may be substituted with deuterium. 6. The method of claim 5,
The naphthalene ring represented by the formula (2) is a 1-naphthyl group or a 2-naphthyl group which is bonded to a phenyl group,
Ar is phenyl, which may be substituted with phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl,
Ar ¹ is phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl, which may be substituted by phenyl, naphthyl or phenanthryl, m is an integer of 0 to 2, Ar ¹ Are the same,
Wherein R is independently methyl, ethyl, n-propyl, isopropyl, t-butyl or cyclohexyl, a is 0 or 1, b is 0 or 1, c is 0 and d is 0 material. 6. The method of claim 5,
Wherein the anthracene compound represented by the general formula (2) is a compound having the following structure.

A material for a light emitting layer containing an anthracene compound represented by the following general formula (3).

The phenanthrene ring represented by the formula (3) is a 2-, 3- or 9-phenanthryl group which is bonded to a phenyl group,
Ar is an aryl having 6 to 18 carbon atoms, which may be substituted with aryl having 6 to 18 carbon atoms, n is 1 or 2, and when n is 1, Ar is bonded to the x position, and when n is 2 Ar is bonded to both the x position and the y position,
Ar ¹ is an aryl having 6 to 18 carbon atoms, which may be substituted with aryl having 6 to 18 carbon atoms, m is an integer from 0 to 2, m has a structure of Ar ¹ when m is 2,
R is independently an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 3 to 6 carbon atoms, a is an integer of 0 to 2, b is 0 or 1, c is an integer of 0 to 2, and d is 0 Is an integer of 2 to 2,
At least one hydrogen in the anthracene compound represented by the formula (3) may be substituted with deuterium. 9. The method of claim 8,
The phenanthrene ring represented by the formula (3) is a 9-phenanthryl group bonded to a phenyl group,
Ar is phenyl, naphthyl, phenanthryl or triphenylenyl, which may be substituted with phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl, n is 1 or 2, and when n is 1 Ar is bonded to the x position, and when n is 2, Ar is bonded to both the x position and the y position,
Ar ¹ is phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl, which may be substituted by phenyl, naphthyl or phenanthryl, m is an integer of 0 to 2,
Wherein R is independently methyl, ethyl, n-propyl, isopropyl, t-butyl or cyclohexyl, a is 0 or 1, b is 0 or 1, c is 0 and d is 0 material. 10. The method according to claim 8 or 9,
n is 1, and Ar is bonded to the x-position. A material for a light-emitting layer containing an anthracene compound represented by the following general formula (4).

The triphenylene ring represented by the formula (4) is a 1- or 2-triphenylenyl group bonded to a phenyl group,
Ar is an aryl having 6 to 18 carbon atoms, which may be substituted with aryl having 6 to 18 carbon atoms; n is 1 or 2; when n is 1, Ar is bonded to either the x position or the y position; and n In this case, Ar is bonded to both the x-position and the y-position to have the same structure,
Ar ¹ is an aryl having 6 to 18 carbon atoms, which may be substituted with aryl having 6 to 18 carbon atoms, m is an integer from 0 to 2, m has a structure of Ar ¹ when m is 2,
R is independently an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 3 to 6 carbon atoms, a is an integer of 0 to 2, b is 0 or 1, c is an integer of 0 to 2, and d is 0 Is an integer of 2 to 2,
At least one hydrogen in the anthracene compound represented by the formula (4) may be substituted with deuterium. 12. The method of claim 11,
The triphenylene ring represented by the formula (4) is a 2-triphenylenyl group bonded to a phenyl group,
Ar is phenyl, naphthyl, phenanthryl or triphenylenyl, which may be substituted with phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl, n is 1 or 2, and when n is 1 Ar is bonded to either the x position or the y position, and when n is 2, Ar is bonded to both the x position and the y position,
Ar ¹ is phenyl, naphthyl, biphenylyl, phenanthryl or triphenylenyl, which may be substituted by phenyl, naphthyl or phenanthryl, m is an integer of 0 to 2,
R is each independently methyl, ethyl, n-propyl, isopropyl, t-butyl or cyclohexyl, a is 0 or 1, b is 0 or 1, c is 0,
Materials for the light emitting layer. 13. The method according to claim 11 or 12,
n is 1, and Ar is bonded to the x-position. An organic electroluminescent device comprising a pair of electrodes made of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, the light-emitting layer containing the material for the light- An electroluminescent device. 15. The method of claim 14,
Wherein the light emitting layer contains at least one selected from the group consisting of an amine having a stilbene structure, an aromatic amine derivative, and a coumarin derivative. 15. The method of claim 14,
Further, an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, wherein at least one of the electron transport layer and the electron injection layer is a quinolinol-based metal complex, a pyridine derivative, A borane derivative, and a benzimidazole derivative. &Lt; RTI ID = 0.0 &gt; 11. &lt; / RTI &gt; 16. The method of claim 15,
Further, an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, wherein at least one of the electron transport layer and the electron injection layer is a quinolinol-based metal complex, a pyridine derivative, A borane derivative, and a benzimidazole derivative. &Lt; RTI ID = 0.0 &gt; 11. &lt; / RTI &gt; 17. The method of claim 16,
Wherein at least one of the electron transporting layer and the electron injecting layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, an alkali metal halide, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, , A halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal, and an organic complex of a rare earth metal. 18. The method of claim 17,
Wherein at least one of the electron transporting layer and the electron injecting layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, an alkali metal halide, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, , A halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal, and an organic complex of a rare earth metal. A display device comprising the organic electroluminescent device according to claim 14. A lighting device comprising the organic electroluminescent device according to claim 14. delete delete

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